Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Chem. & Pharm. Bull. (Tokyo) called Bromination of pyrimidines by N-bromosuccinimide, Author is Nishiwaki, Tarozaemon, which mentions a compound: 6307-44-4, SMILESS is SC1=CC(C)=NC(N)=N1, Molecular C5H7N3S, Safety of 2-Amino-6-methylpyrimidine-4-thiol.
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.
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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com