The Chemistry of Pyrimidinethiols. III. The Synthesis of Some Substituted Pyrimidinthiols and Some Thiazolo[5,4-D]pyrimidines

Abstract

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 5M hydrochloric acid gave 2,5-diamino-6-mercaptopyrimidin-4-ol hy -drochloride 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.