THE CHEMISTRY OF PYRIMIDINETHIOLS .3. THE SYNTHESIS OF SOME SUBSTITUTED PYRIMIDINTHIOLS AND SOME THIAZOLO[5,4-D]PYRIMIDINES

The preparation of a number of pyrimidinethiols and (substituted)thiopyrimidines has been carried out. The reaction of 5-acetylamino-2-aminopyrimidine-4, 6-diol with phosphorus penta- sulfide in pyridine gave 5-amino-2-methylthiazolo[5, 4-d]pyrimidine-7-thiol which was used to prepare several additional novel pyrimidine derivatives. Hydrolysis of the 4-carboxymethylthio derivative by using 5 m hydrochloric acid gave 2, 5-diamino-6-mercaptopyrimidin-4-ol hydrochloride whilst hydrolysis of 2-methyl-7-methylthiothiazolo[5, 4-d]pyrimidin-5-amine gave the corresponding 4-hydroxy derivative. Several 4-arenecarbonylmethylthio derivatives were recovered unchanged from such hydrolysis reactions. © 1990 ASEG.