The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Bromination of pyrimidines by N-bromosuccinimide》. Authors are Nishiwaki, Tarozaemon.The article about the compound:2-Amino-6-methylpyrimidine-4-thiolcas:6307-44-4,SMILESS:SC1=CC(C)=NC(N)=N1).Category: isothiazole. Through the article, more information about this compound (cas:6307-44-4) is conveyed.
cf. CA 54, 24777h. Pyrimidines having potentially tautomeric groups at the 2-, 4-, or 6-position were brominated preferentially at the 5-position by N-bromosuccinimide (I) in HOAc. Thus, 0.01 mole pyrimidine in 20 ml. HOAc was treated with 0.01 mole I 1 hr. at 100°. The precipitate was collected and crystallized to give N:CR1N:CR2.CBr:CR3 (R1, R2, R3, m.p., and % yield given): OH, OH, H, 295° 59; OH, OH, Me, 248°, 76; H, OH, OH, 264°, 61; NH2, OH, H, 275°, 83; NH2, OH, Me, 249°, 61; NH2, H, H, 239-40°, 62; NH2, Cl, Cl, 235-6°, 63; NH2, Me, Me, 183-4°, 75; NH2, Ph, Me, 125-8°, 70; Cl, Cl, NH2, 155-7°, 79; SMe, OH, H, 252°, 41; SMe, OH, Me, 246°, 21; SMe, OH, NH2, -, 60; SMe, Cl, NH2, 164-5°, 66; SEt, OH, H, 185-7.5°, 47. An ionic mechanism was postulated as yields were improved by addition of AlCl3, FeCl3, SnCl4, and picric acid and not reduced by radical inhibitors. The bromination by I of O- and S-alkylpyrimidines, 1,3,4-trimethyluracil, and 2,4-dichloro-6-methylpyrimidine by this method was not successful.
In some applications, this compound(6307-44-4)Category: isothiazole is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com