Category: 6307-44-4

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Pyrimidines. I. Synthesis of pyrimidinethiols, published in 1961, which mentions a compound: 6307-44-4, mainly applied to , Recommanded Product: 6307-44-4.

cf. CA 54, 6747a. The 9 previously unknown isomers of the 22 possible substituted pyrimidinethiols, containing H, HO, NH2, and SH as substituents were synthesized and methods for preparation of some of the previously reported compounds were improved. Various derivatives of RC:N.CR1:N.CR2:CH (I) were prepared for preliminary screening as antitumor agents. HOCH2CH2OH (200 ml.), 125 g. 4,5-Cl(MeS)C4H2N2, and 200 g. NaSH heated slowly to 100° with frothing and bubbling, the mixture carefully heated to 150° and kept 30 min., the solution poured into 1500 ml. H2O and the boiled, decolorized hot filtrate acidified with AcOH, the precipitate reprecipitated from hot dilute aqueous NH4OH with AcOH gave 85 g. I (R = H, R1 = R2 = SH), converted by concentrated HBr to I (R = R1 = H, R2 = SH). NaHS (42 g.) and 13 g. 4,6,2-Cl(HO)(MeS)C4HN2 in 120 ml. HOCH2CH2OH heated 30 min. at 150°, the cooled mixture poured into 500 ml. H2O and the boiled decolorized solution filtered, acidified with AcOH to pH 5 and the refiltered solution adjusted to pH 1.0 with dilute HCl, the product reprecipitated from solution in dilute NH4OH with HCl, and the product recrystallized from HCONMe2-H2O gave 9.0 g. I (R = OH, R1 = R2 = SH), m. 262-4° (method A). The appropriate chloropyrimidine (60 g.) in 500 ml. absolute alc. refluxed 3 hrs. with 150 g. NaHS, the chilled mixture filtered and the alc. washed precipitate boiled in 1 l. H2O, the decolorized solution filtered, the filtrate acidified and the precipitate recrystallized from the appropriate solvent gave RC:N.CR1: N.CR2:CR3 (II) (method B). In method C the procedure was the same but no precipitate was formed. The light yellow alc. solution was diluted with 1 l. boiling H2O and acidified and the precipitate recrystallized The appropriate chloropyrimidine (40 g.) and 40 g. (H2N)2CS in 500 ml. absolute alc refluxed 2 hrs. the mixture chilled and the precipitated ligroine-washed product purified by reprecipitation and recrystallization gave II (method D). The appropriate chloropyrimidine (35 g.) and 70 g. powd. NaHS in 400 ml. H2O was autoclaved 4 hrs. at 150°/8 atm., the solution boiled and the decolorized solution filtered, acidified with AcOH [for the preparation of I (R = NH2, R1 = SH, R2 = OH)] or dilute HCl [for the preparation of I (R = SH, R1 = R2 = OH)], and the products purified by recrystallization (method E). I (R = NH2, R1 = SH, R2 = OH) (50 g. finely powd. and dried at 100°) refluxed 2 hrs. with 150 g. P2S5 in 1.5 l. dry C5H5N, excess C5H5N evaporated in vacuo and the residue diluted cautiously with 750 ml. H2O, the mixture refluxed 2 hrs. on a steam bath with evolution of H2S, the chilled mixture filtered and adjusted to pH 2, the volume reduced to 33% in vacuo and the cooled concentrate filtered, the residue taken up in dilute NH4OH and the boiled decolorized solution filtered, acidified with dilute HCl and the precipitate recrystallized from HCONMe2-H2O gave 35 g. I (R = H2N, R1 = R2 = SH). Purified P2S5 (125 g.) and 52 g. I (R = R1 = H, R2 = OH) refluxed 1 hr. with stirring in l. C5H5N, the hot solution poured into 1 l. H2O and the solution heated on a steam bath 3 hrs., the filtered solution evaporated in vacuo to 200 ml., refrigerated and the H2O-washed product recrystallized from 500 ml. boiling H2O gave 42 g. I (R = R1 = H, R2 = SH). I(R = R2 = Cl, R1 = NH2) (33 g.) added to 1 l. 4:1 alc.-H2O containing 40 g. NaOH saturated with H2S, the mixture refluxed with stirring 2 hrs. with passage of H2S, treated with C and the filtered solution acidified with AcOH gave 42 g. I (R = SH, R1 = NH2, R2 = Cl), m. 302° (decomposition), λ 260 mμ (ε 9800, pH 1), λ 280 mμ (ε 12,500, pH 11), converted by autoclaving with NaHS to I (R = SH, R1 = R2 = OH). I (R = R2 = OH, R1 = SH)(60 g.)in 1 l. 2N NaOH stirred 3 hrs. with dropwise addition of 50 g. Me2SO4, the solution boiled with addition of C and the decolorized filtered solution acidified to pH 1.0 with HCl gave 50 g. I (R = R1 = OH, R1 = MeS) (III), m. above 360° (H2O). III (80 g.) refluxed 2 hrs. with 500 ml. POCl3, excess POCl3 removed in vacuo and the residue poured with stirring over crushed ice, the mixture stirred 20 min. at 0°, filtered and the precipitate washed in ice H2O until the pH of the washings was no longer below 5, the material dried 16 hrs. in vacuo and recrystallized from MeOH and H2O gave 64 g. I (R = R2 = Cl, R1 = MeS) (IV), m 43°. Treatment of IV with NaHS at 150° in HOCH2CH2OH gave I (R = R1 = R2 = SH). NaHS (75 g.) in 500 ml. MeOH at 50° stirred with portionwise addition of 50 g. IV, the mixture stirred 30 min. before dilution with 1 l. H2O, the solution boiled with C and the filtered solution acidified, the product reprecipitated from dilute NH4OH with AcOH, and recrystallized from HCONMe2-H2O gave 40 g. I (R = R2 = HS, R1 = MeS), m. above 360°. IV (50 g.) refluxed with stirring 4 hrs. in 500 ml. 2N NaOH, the solution decolorized and the filtered solution acidified with AcOH, the precipitate purified by reprecipitation and recrystallized from HCONMe2-H2O gave 40 g. I (R = Cl, R1 = MeS, R2 = OH), m. 208°. Absolute MeOH (150 ml.) at 0° treated with 30 g. finely powd. IV, the mixture stirred 45 min. with passage of dry Cl, filtered from 8 g. product, and the filtrate evaporated at 20° in a stream of dry air gave 12 g. product; the crops combined and recrystallized from EtOAc and C7H16 gave 17 g. I (R = R2 = Cl, R1 = MeSO2) (V), m. 119°. V (15 g.) warmed in 200 ml. N NaOH, the filtered solution chilled and the precipitate washed with cold H2O and alc., the dry salt (11.6 g.) in 150 ml. H2O carefully neutralized with HCl and the solution evaporated in vacuo, the residue taken up in boiling Me2CHOH and diluted with C7H16 gave 5 g. I (R = R2 = Cl, R1 = OH), m. 262° (Me2CHOHC7H16). The ultraviolet absorption spectra of the completed series of I showed the approx. maximum of the major peak of I in solutions at pH 1.0 were 280, 300-20, 320-40, and 360-70 mμ for 2-pyrimidinethiols, 4-pyrimidinethiols, 2,4-pyrimidinedithiols, and 4,6-pyrimidinedithiols, resp. Data for I and for a number of known thiopyrimidines, II, not previously published are recorded for comparison [R, R1, R2, R3, m.p. (solvents), and % yield given]: H, SH, H, H, 229-30° (alc.), 70; H, H, SH, H, 190-2° (H2O), 69; H, OH, SH, H, 298-300° (H2O-HCONMe2), 88; H, SH, OH, H, 310-12° (H2O), 73; H, NH2, SH, H, 231-3° (H2O-HCONMe2), 68; OH, H, SH, H, 247° (H2O), 79; H2N, H, SH, H, 306° (H2O-HCONMe2), 61; H, SH, SH, H, 300° (H2O), 70; HS, H, SH, H, 250-2° (H2O), 70; OH, SH, OH, H, above 360° (H2O-HCONMe2), 84; OH, OH, SH, H, 245° (H2O), 54; H2N, OH, SH, H, 355° (H2O-HCONMe2), 43; OH, H2N, SH, H, above 360° (H2O-HCONMe2), 82; H2N, H2N, SH, H, above 360° (reprecipitation), 50; H2N, SH, OH, H, above 360° (reprecipitation), 91; H2N, SH, H2N, H, above 360° (reprecipitation), 93; OH, SH, SH, H, 262-4° (H2O-HCONMe2), 79; H2N, SH, SH, H, above 360° (H2O-HCONMe2), 60; SH, OH, SH, H, 266-7° (H2O-HCONMe2), 46; SH, H2N, SH, H, 267° (H2O), 76; SH, SH, SH, H, above 360° (reprecipitation), 70; Cl, H2N, H, Cl, above 360° (reprecipitation), 63; Me, H2N, SH, H, 321° (reprecipitation), 84; Me, H2N, SH, Br, 207° (H2O-HCONMe2), 98; Me, SH, SH, H, above 360° (H2O-HCONMe2), 70; H, SH, SH, CO2H, 261-3° (H2O-HCONMe2), 63; SH, H, SH, Cl, 215-17° (reprecipitation), 70; SH, H, SH, Br, 213° (reprecipitation), 92; SH, H2N, SH, Ph, 266-8° (H2O-HCONMe2), 60; H, MeS, SH, H, 203° (H2O-HCONMe2), 96; Me, MeS, SH, H, 239° (H2O-HCONMe2), 78; SH, MeS, SH, H, above 360° (H2O-alc.), 80. For comparison of structure and biol. activities in pyrimidine thiols, a number of new related 4-pyrimidine thiols substituted in position 5 were synthesized. Thiopyrimidine (0.08 mole) stirred in 250 ml. N NaOH treated with a stoichiometric amount of the appropriate alkyl halide, the mixture stirred 3 hrs. and the H2O-washed precipitate recrystallized gave the corresponding alkylthiopyrimidine (method A). Similarly, the above reaction mixture on failure to give a precipitate was acidified with AcOH and the product recrystallized to yield the required alkyl thiopyrimidine (method B). The yields ranged from 80 to 95%. Phys. data for alkylthio- and aralkylthiopyrimidines are listed [R, R1, R2, R3 of formula II, method of synthesis, m.p. (solvent, if other than HCONMe2 + H2O) given]: MeS, H, OH, H, B, 230° (H2O); PhCH2S, H, OH, H, B, 238-9°; 2,4-Cl2C6H3CH2S, H, OH, H, B, 191.3°; MeS, H, H2 N, H, A, 168-70°; EtS, H, H2N, H, A, 147-9°; PhCH2S, H, H2N, H, A, 140°; 2,4-Cl2C6H3CH2S, H, H2N, H, A, 184-6°; p-O2NC6H4CH2S, H, H2N, H, A, 165-7°; MeS, H, MeS, H, A, 52-4° (C7H16); MeS, H, MeS, H2N, A, 79°; MeS, H, MeS, Cl, A, 118-20°; EtS, H, EtS, Cl, A, 58-9°; PhCH2S, H, PhCH2S, Cl, A, 86-8°; 2,4-Cl2C6H3CH2S, H 2,4-Cl2C6H3CH2S, Cl, A, 155°; MeS, H, MeS, Br, A, 155°; PrS, H, PrS, Br, A, 44-6°; PhCH2S, H, PhCH2S, Br, A, 95-7°; 2,4-Cl2C6H3CH2S, H, 2,4-Cl2C6H3CH2S, Br, A, 149°; p-O2NC6H4CH2S, H, p-O2NC6H4CH2S, Br, A, 168-70°; PhCH2S, OH, OH, H, B, 242°; H, OH, o-ClC6H4CH2S, H, A, 174-6°; H, OH, 2,4-Cl2C6H3CH2S, H, A, 193-4°; MeS, H2N, H, H, A, 150-3°; Et, H2N, H, H, A, 155°; PhCH2S, H2N, H, H, A, 178-80°; 2,4-Cl2C6H3CH2S, H2N, H, H, A, 155-7°; o-ClC6H4CH2S, H2N, Me, H, A, 143-5°; MeS, H2N, Cl, H, A, 106-8°; EtS, H2N, Cl, H, A, 109-10°; PrS, H2N, Cl, H, A, 105-6°; PrS, H2N, Me, Br, A, 95-7°; o-ClC6H4CH2S, H2N, Me, Br, A, 138-40°; p-O2NC6H4CH2S, H2N, Me, Br, A, 226-8°; EtS, H2N, EtS, H, A, 54°; PrS, H2N, PrS, H, A, 85-7°; PhCH2S, H2N, PhCH2S, H, A, 134-6°; 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, H, A, 159-61°; MeS, H2N, MeS, Ph, A, 128-9° (C7H15); PhCH2S, H2N, PhCH2S, Ph, A, 207-9° (C7H15); o-ClC6H4CH2S, H2N, o-ClC6H4CH2S, Ph, A, 174-5° (EtOAc); 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, Ph, A, 164-7° (PhMe); MeS, MeS, Me, H, A, 43-5° (C7H15); 2,4-Cl2C6H3CH2S, MeS, Me, H, A, 100-2°; H2N, MeS, MeS, H, A, 121-3°; MeS, MeS, MeS, H, A, 114-16°; H, MeS, MeS, CO2H, B, 201-3°; PhCH2S, PhCH2S, Me, H, A, 37-9° (C7H15); o-ClC6H4CH2S, o-ClC6H4CH2S, o-ClC6H4CH2S, H, A, 117-18° (H2O-alc.); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, H, A, 94-6° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, Me, H, A, 107-9° (C7H15); H2N, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 125-7° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 120-4°. Other II prepared were (R, R1, R2, R3, method of synthesis, and m.p. (solvent) given): MeS, OH, H2N, H, B, 294° (H2O); MeS, H2N, Me, H, A, 152°; EtS, H2N, Me, H, A, 122-4°; BuS, H2N, Me, H, A, 70-2°; PhCH2S, H2N, Me, H, A, 118-20°; 2,4-Cl2C6H3CH2S, H2N, Me, H, A, 157-60°; p-O2NC6H4CH2S, H2N, Me, H, A, 157-9°; MeS, H2N, OH, H, B, 274-6°; EtS, H2N, OH, H, B, 248°; PrS, H2N, OH, H, B, 228-32°; BuS, H2N, OH, H, B, 240-2°; C6H11S, H2N, OH, H, B, 185°; MeS, H2N, Me, Br, A, 140-2°; PhCH2S, H2N, Me, Br, A, 135-7°; MeS, H2N, MeS, H, A, 116-18°; OH, MeS, MeS, H, B, 197° (H2O). Ultraviolet maximum at pH 1 and 11 were given for the II prepared

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Amino-6-methylpyrimidine-4-thiol( cas:6307-44-4 ) is researched.Quality Control of 2-Amino-6-methylpyrimidine-4-thiol.Felczak, Krzysztof; Bretner, Maria; Kulikowski, Tadeusz; Shugar, David published the article 《High-yield regioselective thiation of biologically important pyrimidinones, dihydropyrimidinones and their ribo, 2′-deoxyribo and 2′,3′-dideoxyribo nucleosides》 about this compound( cas:6307-44-4 ) in Nucleosides & Nucleotides. Keywords: pyrimidinone regioselective thiation Lawesson reagent; nucleoside pyrimidinone regioselective thiation Lawesson reagent. Let’s learn more about this compound (cas:6307-44-4).

Convenient and high-yield regioselective thiation procedures based on the use of the Lawesson reagent in different solvents, are described for conversion of the 2- and 4-keto, and 2,4-diketo pyrimidines to the corresponding 2(4)-thio, and 2,4-dithio, derivatives This method is applicable to thiation of the 4-keto groups of 5,6-dihydropyrimidinones and pyrimidine nucleosides. The mild reaction conditions employed are such that it is the method of choice for compounds with labile glycosidic bonds, of choice for compounds with labile glycosidic bonds, such as 5,6-dihydropyrimidine nucleosides and the 2′,3′-dideoxynucleosides currently of interest as antiretroviral, including anti-HIV, agents.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Erkin, A. V.; Krutikov, V. I. published the article 《N-(3-Sulfanylmethyl-4H-1,2,4-triazol-4-yl)-2-sulfanylacetamide Containing Terminal 2-Amino-6-methylpyrimidin-4-yl Fragments. Synthesis from 2-[(2-Amino-6-methylpyrimidin-4-yl)sulfanyl]acetohydrazide and Triethyl Orthoformate》. Keywords: amino methylpyrimidinyl sulfanylacetohydrazide preparation triethyl orthoformate heterocyclization; methyl aminopyrimidinyl sulfanylmethyltriazoloacetamide preparation.They researched the compound: 2-Amino-6-methylpyrimidine-4-thiol( cas:6307-44-4 ).SDS of cas: 6307-44-4. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6307-44-4) here.

2-[(2-Amino-6-methylpyrimidin-4-yl)sulfanyl]acetohydrazide reacted with tri-Et orthoformate at a molar ratio of 1:1 to give 2-[(2-amino-6-methylpyrimidin-4-yl)sulfanyl]-N-{3-[(2-amino-6-methylpyrimidin-4-yl)sulfanylmethyl]-4H-1,2,4-triazol-4-yl}acetamide.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 6307-44-4, is researched, Molecular C5H7N3S, about Guanine phosphoribosyltransferase from Escherichia coli. Specificity and properties, the main research direction is guanine phosphoribosyltransferase purine substrate; hypoxanthine guanine phosphoribosyltransferase.COA of Formula: C5H7N3S.

The specificity and properties of a novel guanine phosphoribosyltransferase of E. coli were studied and compared to those of the hypoxanthine-guanine phosphoribosyltransferase from other sources. The structural requirements for binding of purines to this enzyme were explored by the determination of the Ki values for 100 purines and purine analogs. The most effective binding occurred when the purine contained an oxo or SH group in the 6 position and an NH2 or OH group in the 2 position. Unlike the hypoxanthine-guanine phosphoribosyltransferase from other sources, this enzyme bound hypoxanthine 67 times less effectively than guanine and 4 times less effectively than xanthine. Rates of nucleotide formation from a number of purines and purine analogs were also determined The enzyme had a pH optimum from 7.4 to 8.2. From secondary double-reciprocal plots derived from an initial velocity anal., the Km values were 0.037mM for guanine and 0.33mM for 5-phosphoribosyl 1-pyrophosphate. The enzyme was sensitive to inhibition by p-chloromercuribenzoate, and this inhibition could be reversed by either dithiothreitol or β-mercaptoethanol. The apparent activation energy with guanine as substrate was 12,800 cal/mole below 23° and 3370 cal/mole above 23°. Using isoelec. focusing, the guanine phosphoribosyltransferase had an apparent pI of 5.50, while the pI of a 2nd enzyme which was specific for hypoxanthine was 4.8.

In addition to the literature in the link below, there is a lot of literature about this compound(2-Amino-6-methylpyrimidine-4-thiol)COA of Formula: C5H7N3S, illustrating the importance and wide applicability of this compound(6307-44-4).

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Pyrimidines. I. Synthesis of pyrimidinethiols, published in 1961, which mentions a compound: 6307-44-4, mainly applied to , Recommanded Product: 6307-44-4.

cf. CA 54, 6747a. The 9 previously unknown isomers of the 22 possible substituted pyrimidinethiols, containing H, HO, NH2, and SH as substituents were synthesized and methods for preparation of some of the previously reported compounds were improved. Various derivatives of RC:N.CR1:N.CR2:CH (I) were prepared for preliminary screening as antitumor agents. HOCH2CH2OH (200 ml.), 125 g. 4,5-Cl(MeS)C4H2N2, and 200 g. NaSH heated slowly to 100° with frothing and bubbling, the mixture carefully heated to 150° and kept 30 min., the solution poured into 1500 ml. H2O and the boiled, decolorized hot filtrate acidified with AcOH, the precipitate reprecipitated from hot dilute aqueous NH4OH with AcOH gave 85 g. I (R = H, R1 = R2 = SH), converted by concentrated HBr to I (R = R1 = H, R2 = SH). NaHS (42 g.) and 13 g. 4,6,2-Cl(HO)(MeS)C4HN2 in 120 ml. HOCH2CH2OH heated 30 min. at 150°, the cooled mixture poured into 500 ml. H2O and the boiled decolorized solution filtered, acidified with AcOH to pH 5 and the refiltered solution adjusted to pH 1.0 with dilute HCl, the product reprecipitated from solution in dilute NH4OH with HCl, and the product recrystallized from HCONMe2-H2O gave 9.0 g. I (R = OH, R1 = R2 = SH), m. 262-4° (method A). The appropriate chloropyrimidine (60 g.) in 500 ml. absolute alc. refluxed 3 hrs. with 150 g. NaHS, the chilled mixture filtered and the alc. washed precipitate boiled in 1 l. H2O, the decolorized solution filtered, the filtrate acidified and the precipitate recrystallized from the appropriate solvent gave RC:N.CR1: N.CR2:CR3 (II) (method B). In method C the procedure was the same but no precipitate was formed. The light yellow alc. solution was diluted with 1 l. boiling H2O and acidified and the precipitate recrystallized The appropriate chloropyrimidine (40 g.) and 40 g. (H2N)2CS in 500 ml. absolute alc refluxed 2 hrs. the mixture chilled and the precipitated ligroine-washed product purified by reprecipitation and recrystallization gave II (method D). The appropriate chloropyrimidine (35 g.) and 70 g. powd. NaHS in 400 ml. H2O was autoclaved 4 hrs. at 150°/8 atm., the solution boiled and the decolorized solution filtered, acidified with AcOH [for the preparation of I (R = NH2, R1 = SH, R2 = OH)] or dilute HCl [for the preparation of I (R = SH, R1 = R2 = OH)], and the products purified by recrystallization (method E). I (R = NH2, R1 = SH, R2 = OH) (50 g. finely powd. and dried at 100°) refluxed 2 hrs. with 150 g. P2S5 in 1.5 l. dry C5H5N, excess C5H5N evaporated in vacuo and the residue diluted cautiously with 750 ml. H2O, the mixture refluxed 2 hrs. on a steam bath with evolution of H2S, the chilled mixture filtered and adjusted to pH 2, the volume reduced to 33% in vacuo and the cooled concentrate filtered, the residue taken up in dilute NH4OH and the boiled decolorized solution filtered, acidified with dilute HCl and the precipitate recrystallized from HCONMe2-H2O gave 35 g. I (R = H2N, R1 = R2 = SH). Purified P2S5 (125 g.) and 52 g. I (R = R1 = H, R2 = OH) refluxed 1 hr. with stirring in l. C5H5N, the hot solution poured into 1 l. H2O and the solution heated on a steam bath 3 hrs., the filtered solution evaporated in vacuo to 200 ml., refrigerated and the H2O-washed product recrystallized from 500 ml. boiling H2O gave 42 g. I (R = R1 = H, R2 = SH). I(R = R2 = Cl, R1 = NH2) (33 g.) added to 1 l. 4:1 alc.-H2O containing 40 g. NaOH saturated with H2S, the mixture refluxed with stirring 2 hrs. with passage of H2S, treated with C and the filtered solution acidified with AcOH gave 42 g. I (R = SH, R1 = NH2, R2 = Cl), m. 302° (decomposition), λ 260 mμ (ε 9800, pH 1), λ 280 mμ (ε 12,500, pH 11), converted by autoclaving with NaHS to I (R = SH, R1 = R2 = OH). I (R = R2 = OH, R1 = SH)(60 g.)in 1 l. 2N NaOH stirred 3 hrs. with dropwise addition of 50 g. Me2SO4, the solution boiled with addition of C and the decolorized filtered solution acidified to pH 1.0 with HCl gave 50 g. I (R = R1 = OH, R1 = MeS) (III), m. above 360° (H2O). III (80 g.) refluxed 2 hrs. with 500 ml. POCl3, excess POCl3 removed in vacuo and the residue poured with stirring over crushed ice, the mixture stirred 20 min. at 0°, filtered and the precipitate washed in ice H2O until the pH of the washings was no longer below 5, the material dried 16 hrs. in vacuo and recrystallized from MeOH and H2O gave 64 g. I (R = R2 = Cl, R1 = MeS) (IV), m 43°. Treatment of IV with NaHS at 150° in HOCH2CH2OH gave I (R = R1 = R2 = SH). NaHS (75 g.) in 500 ml. MeOH at 50° stirred with portionwise addition of 50 g. IV, the mixture stirred 30 min. before dilution with 1 l. H2O, the solution boiled with C and the filtered solution acidified, the product reprecipitated from dilute NH4OH with AcOH, and recrystallized from HCONMe2-H2O gave 40 g. I (R = R2 = HS, R1 = MeS), m. above 360°. IV (50 g.) refluxed with stirring 4 hrs. in 500 ml. 2N NaOH, the solution decolorized and the filtered solution acidified with AcOH, the precipitate purified by reprecipitation and recrystallized from HCONMe2-H2O gave 40 g. I (R = Cl, R1 = MeS, R2 = OH), m. 208°. Absolute MeOH (150 ml.) at 0° treated with 30 g. finely powd. IV, the mixture stirred 45 min. with passage of dry Cl, filtered from 8 g. product, and the filtrate evaporated at 20° in a stream of dry air gave 12 g. product; the crops combined and recrystallized from EtOAc and C7H16 gave 17 g. I (R = R2 = Cl, R1 = MeSO2) (V), m. 119°. V (15 g.) warmed in 200 ml. N NaOH, the filtered solution chilled and the precipitate washed with cold H2O and alc., the dry salt (11.6 g.) in 150 ml. H2O carefully neutralized with HCl and the solution evaporated in vacuo, the residue taken up in boiling Me2CHOH and diluted with C7H16 gave 5 g. I (R = R2 = Cl, R1 = OH), m. 262° (Me2CHOHC7H16). The ultraviolet absorption spectra of the completed series of I showed the approx. maximum of the major peak of I in solutions at pH 1.0 were 280, 300-20, 320-40, and 360-70 mμ for 2-pyrimidinethiols, 4-pyrimidinethiols, 2,4-pyrimidinedithiols, and 4,6-pyrimidinedithiols, resp. Data for I and for a number of known thiopyrimidines, II, not previously published are recorded for comparison [R, R1, R2, R3, m.p. (solvents), and % yield given]: H, SH, H, H, 229-30° (alc.), 70; H, H, SH, H, 190-2° (H2O), 69; H, OH, SH, H, 298-300° (H2O-HCONMe2), 88; H, SH, OH, H, 310-12° (H2O), 73; H, NH2, SH, H, 231-3° (H2O-HCONMe2), 68; OH, H, SH, H, 247° (H2O), 79; H2N, H, SH, H, 306° (H2O-HCONMe2), 61; H, SH, SH, H, 300° (H2O), 70; HS, H, SH, H, 250-2° (H2O), 70; OH, SH, OH, H, above 360° (H2O-HCONMe2), 84; OH, OH, SH, H, 245° (H2O), 54; H2N, OH, SH, H, 355° (H2O-HCONMe2), 43; OH, H2N, SH, H, above 360° (H2O-HCONMe2), 82; H2N, H2N, SH, H, above 360° (reprecipitation), 50; H2N, SH, OH, H, above 360° (reprecipitation), 91; H2N, SH, H2N, H, above 360° (reprecipitation), 93; OH, SH, SH, H, 262-4° (H2O-HCONMe2), 79; H2N, SH, SH, H, above 360° (H2O-HCONMe2), 60; SH, OH, SH, H, 266-7° (H2O-HCONMe2), 46; SH, H2N, SH, H, 267° (H2O), 76; SH, SH, SH, H, above 360° (reprecipitation), 70; Cl, H2N, H, Cl, above 360° (reprecipitation), 63; Me, H2N, SH, H, 321° (reprecipitation), 84; Me, H2N, SH, Br, 207° (H2O-HCONMe2), 98; Me, SH, SH, H, above 360° (H2O-HCONMe2), 70; H, SH, SH, CO2H, 261-3° (H2O-HCONMe2), 63; SH, H, SH, Cl, 215-17° (reprecipitation), 70; SH, H, SH, Br, 213° (reprecipitation), 92; SH, H2N, SH, Ph, 266-8° (H2O-HCONMe2), 60; H, MeS, SH, H, 203° (H2O-HCONMe2), 96; Me, MeS, SH, H, 239° (H2O-HCONMe2), 78; SH, MeS, SH, H, above 360° (H2O-alc.), 80. For comparison of structure and biol. activities in pyrimidine thiols, a number of new related 4-pyrimidine thiols substituted in position 5 were synthesized. Thiopyrimidine (0.08 mole) stirred in 250 ml. N NaOH treated with a stoichiometric amount of the appropriate alkyl halide, the mixture stirred 3 hrs. and the H2O-washed precipitate recrystallized gave the corresponding alkylthiopyrimidine (method A). Similarly, the above reaction mixture on failure to give a precipitate was acidified with AcOH and the product recrystallized to yield the required alkyl thiopyrimidine (method B). The yields ranged from 80 to 95%. Phys. data for alkylthio- and aralkylthiopyrimidines are listed [R, R1, R2, R3 of formula II, method of synthesis, m.p. (solvent, if other than HCONMe2 + H2O) given]: MeS, H, OH, H, B, 230° (H2O); PhCH2S, H, OH, H, B, 238-9°; 2,4-Cl2C6H3CH2S, H, OH, H, B, 191.3°; MeS, H, H2 N, H, A, 168-70°; EtS, H, H2N, H, A, 147-9°; PhCH2S, H, H2N, H, A, 140°; 2,4-Cl2C6H3CH2S, H, H2N, H, A, 184-6°; p-O2NC6H4CH2S, H, H2N, H, A, 165-7°; MeS, H, MeS, H, A, 52-4° (C7H16); MeS, H, MeS, H2N, A, 79°; MeS, H, MeS, Cl, A, 118-20°; EtS, H, EtS, Cl, A, 58-9°; PhCH2S, H, PhCH2S, Cl, A, 86-8°; 2,4-Cl2C6H3CH2S, H 2,4-Cl2C6H3CH2S, Cl, A, 155°; MeS, H, MeS, Br, A, 155°; PrS, H, PrS, Br, A, 44-6°; PhCH2S, H, PhCH2S, Br, A, 95-7°; 2,4-Cl2C6H3CH2S, H, 2,4-Cl2C6H3CH2S, Br, A, 149°; p-O2NC6H4CH2S, H, p-O2NC6H4CH2S, Br, A, 168-70°; PhCH2S, OH, OH, H, B, 242°; H, OH, o-ClC6H4CH2S, H, A, 174-6°; H, OH, 2,4-Cl2C6H3CH2S, H, A, 193-4°; MeS, H2N, H, H, A, 150-3°; Et, H2N, H, H, A, 155°; PhCH2S, H2N, H, H, A, 178-80°; 2,4-Cl2C6H3CH2S, H2N, H, H, A, 155-7°; o-ClC6H4CH2S, H2N, Me, H, A, 143-5°; MeS, H2N, Cl, H, A, 106-8°; EtS, H2N, Cl, H, A, 109-10°; PrS, H2N, Cl, H, A, 105-6°; PrS, H2N, Me, Br, A, 95-7°; o-ClC6H4CH2S, H2N, Me, Br, A, 138-40°; p-O2NC6H4CH2S, H2N, Me, Br, A, 226-8°; EtS, H2N, EtS, H, A, 54°; PrS, H2N, PrS, H, A, 85-7°; PhCH2S, H2N, PhCH2S, H, A, 134-6°; 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, H, A, 159-61°; MeS, H2N, MeS, Ph, A, 128-9° (C7H15); PhCH2S, H2N, PhCH2S, Ph, A, 207-9° (C7H15); o-ClC6H4CH2S, H2N, o-ClC6H4CH2S, Ph, A, 174-5° (EtOAc); 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, Ph, A, 164-7° (PhMe); MeS, MeS, Me, H, A, 43-5° (C7H15); 2,4-Cl2C6H3CH2S, MeS, Me, H, A, 100-2°; H2N, MeS, MeS, H, A, 121-3°; MeS, MeS, MeS, H, A, 114-16°; H, MeS, MeS, CO2H, B, 201-3°; PhCH2S, PhCH2S, Me, H, A, 37-9° (C7H15); o-ClC6H4CH2S, o-ClC6H4CH2S, o-ClC6H4CH2S, H, A, 117-18° (H2O-alc.); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, H, A, 94-6° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, Me, H, A, 107-9° (C7H15); H2N, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 125-7° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 120-4°. Other II prepared were (R, R1, R2, R3, method of synthesis, and m.p. (solvent) given): MeS, OH, H2N, H, B, 294° (H2O); MeS, H2N, Me, H, A, 152°; EtS, H2N, Me, H, A, 122-4°; BuS, H2N, Me, H, A, 70-2°; PhCH2S, H2N, Me, H, A, 118-20°; 2,4-Cl2C6H3CH2S, H2N, Me, H, A, 157-60°; p-O2NC6H4CH2S, H2N, Me, H, A, 157-9°; MeS, H2N, OH, H, B, 274-6°; EtS, H2N, OH, H, B, 248°; PrS, H2N, OH, H, B, 228-32°; BuS, H2N, OH, H, B, 240-2°; C6H11S, H2N, OH, H, B, 185°; MeS, H2N, Me, Br, A, 140-2°; PhCH2S, H2N, Me, Br, A, 135-7°; MeS, H2N, MeS, H, A, 116-18°; OH, MeS, MeS, H, B, 197° (H2O). Ultraviolet maximum at pH 1 and 11 were given for the II prepared

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Hurst, Derek T.; Beaumont, Claire; Jones, Derek T. E.; Kingsley, Deborah A.; Partridge, Julian D.; Rutherford, Trevor J. researched the compound: 2-Amino-6-methylpyrimidine-4-thiol( cas:6307-44-4 ).SDS of cas: 6307-44-4.They published the article 《The chemistry of pyrimidinethiols. II. The preparation and reactions of some 2-arenecarbonylmethylthiopyrimidines》 about this compound( cas:6307-44-4 ) in Australian Journal of Chemistry. Keywords: pyrimidinone phenacylthio; phenacylthiopyrimidinone. We’ll tell you more about this compound (cas:6307-44-4).

2-Pyrimidinethiones were treated with phenacyl halides to give (phenacylthio)pyrimidines I (R1= Ph, tolyl, halophenyl, anisyl, dimethyoxyphenyl, O2NC6H4, biphenyl, Cl2C6H3, naphthyl; R2 = Me, H, Ph, Pr, NH2). Some I were heated in Ph2O to give phenacylidenepyrimidinones II (R3 = Ph, tolyl, halophenyl, anisyl, dimethyoxyphenyl, O2NC6H4, biphenylyl, naphthyl; R4 = Me, H, Pr).

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Amino-6-methylpyrimidine-4-thiol, is researched, Molecular C5H7N3S, CAS is 6307-44-4, about Inhibition studies of Pyrimidine class of compounds on Enoyl-ACP reductase enzyme.Application In Synthesis of 2-Amino-6-methylpyrimidine-4-thiol.

Present work is aimed to identify and understand the inhibiting nature of Pyrimidine class of compounds to enoyl acyl carrier protein reductase (Enoyl-ACP reductase), which is one of the main receptor proteins used in drug discovery for screening anti-leprosy agents. Series of Pyrimidine based compounds are virtually designed using the mol. mechanic technique. The designed mols. were docked using with crystal structure of Enoyl-ACP reductase (PDB ID: 2NTV) using Autodock mol. docking software. The method uses rigid-protein and flexible ligand-techniques to acquire maximum conformations of ligand mols. The docking results were evaluated using the acquired binding energy values for each ligand-protein complex. Those mols. having higher neg. binding energy values with higher hydrogen bonds are selected for further anal. The selected mols. show better hydrophobic, electrostatic and steric interactions with receptor protein. It is reported that the presence of -CH2OH at R1 and -C6H5 at R2 and R3 positions enhance the neg. binding energy (ΔG kcal mol-1) values. Particularly -OC6H5 at R1 and -OH at R2 help in increasing the interactions between ligand and protein. The results show the mol. level interactions and inhibit the receptor protein.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 6307-44-4, is researched, SMILESS is SC1=CC(C)=NC(N)=N1, Molecular C5H7N3SJournal, Russian Journal of General Chemistry called Quantum Chemistry, NMR Spectroscopy, and Single-Crystal Diffractometry Methods in the Analysis of Protonation Pathways of 2-Amino-4-benzylsulfanyl-6-methylpyrimidines, Author is Erkin, A. V.; Gurzhiy, V. V.; Krutikov, V. I.; Neporozhneva, O. V., the main research direction is aminomethyl pyrimidinethione benzyl chloride protonation mechanism NMR chem shift.Category: isothiazole.

Protonation pathways of 2-amino-4-benzylsulfanyl-6-methylpyrimidines have been investigated by means of semiempirical PM3 quantum-chem. simulation, 13C NMR spectroscopy, and single-crystal diffractometry methods. In the gas phase and in the bipolar aprotic solvent, the protonation involves the N1 atom. The protonation in the crystalline state is characterized by the formation of a branched system of H-bonds, involving the protons of the amino group besides the mentioned nitrogen atom.

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Computed Properties of C5H7N3S. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Amino-6-methylpyrimidine-4-thiol, is researched, Molecular C5H7N3S, CAS is 6307-44-4, about Guanine phosphoribosyltransferase from Escherichia coli. Specificity and properties. Author is Miller, Richard L.; Ramsey, Gwendolyn A.; Krenitsky, Thomas A.; Elion, Gertrude B..

The specificity and properties of a novel guanine phosphoribosyltransferase of E. coli were studied and compared to those of the hypoxanthine-guanine phosphoribosyltransferase from other sources. The structural requirements for binding of purines to this enzyme were explored by the determination of the Ki values for 100 purines and purine analogs. The most effective binding occurred when the purine contained an oxo or SH group in the 6 position and an NH2 or OH group in the 2 position. Unlike the hypoxanthine-guanine phosphoribosyltransferase from other sources, this enzyme bound hypoxanthine 67 times less effectively than guanine and 4 times less effectively than xanthine. Rates of nucleotide formation from a number of purines and purine analogs were also determined The enzyme had a pH optimum from 7.4 to 8.2. From secondary double-reciprocal plots derived from an initial velocity anal., the Km values were 0.037mM for guanine and 0.33mM for 5-phosphoribosyl 1-pyrophosphate. The enzyme was sensitive to inhibition by p-chloromercuribenzoate, and this inhibition could be reversed by either dithiothreitol or β-mercaptoethanol. The apparent activation energy with guanine as substrate was 12,800 cal/mole below 23° and 3370 cal/mole above 23°. Using isoelec. focusing, the guanine phosphoribosyltransferase had an apparent pI of 5.50, while the pI of a 2nd enzyme which was specific for hypoxanthine was 4.8.

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Safety of 2-Amino-6-methylpyrimidine-4-thiol. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Amino-6-methylpyrimidine-4-thiol, is researched, Molecular C5H7N3S, CAS is 6307-44-4, about Inhibition studies of Pyrimidine class of compounds on Enoyl-ACP reductase enzyme. Author is Ganatra, Sunil H.; Bodhe, Manoj N.; Tatode, P. N..

Present work is aimed to identify and understand the inhibiting nature of Pyrimidine class of compounds to enoyl acyl carrier protein reductase (Enoyl-ACP reductase), which is one of the main receptor proteins used in drug discovery for screening anti-leprosy agents. Series of Pyrimidine based compounds are virtually designed using the mol. mechanic technique. The designed mols. were docked using with crystal structure of Enoyl-ACP reductase (PDB ID: 2NTV) using Autodock mol. docking software. The method uses rigid-protein and flexible ligand-techniques to acquire maximum conformations of ligand mols. The docking results were evaluated using the acquired binding energy values for each ligand-protein complex. Those mols. having higher neg. binding energy values with higher hydrogen bonds are selected for further anal. The selected mols. show better hydrophobic, electrostatic and steric interactions with receptor protein. It is reported that the presence of -CH2OH at R1 and -C6H5 at R2 and R3 positions enhance the neg. binding energy (ΔG kcal mol-1) values. Particularly -OC6H5 at R1 and -OH at R2 help in increasing the interactions between ligand and protein. The results show the mol. level interactions and inhibit the receptor protein.

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