Synthesis of Potential Anticancer Agents. IV. 5,7-Disubstituted s-Triazolo[2,3-a]pyrimidines

Abstract

The products of the condensation of 5-amino-s-triazole (I) with ethyl maionate, ethyl cyanoacetate, and methyl ethoxycarbonyldithioacetate were proved to be respectively 5,7-dihydroxy-, 5-hydroxy-7-amino-, and 5-hydroxy-7-mercapto-s-triazolo[2,3-a]pyriminines (II, III, and IV). (II) was converted into the 5,7-dichloro derivative (VI), and the reactivity of the two halogens in (VI) towards the usual nucleophilic reagents was examined. (IV) was also transformed into the 5-chloro-7-methylthio derivative (XXI), which was converted into 5-substituted 7-methylthio derivatives by nucleophilic substitution. Ultraviolet absorption spectra of 5-substituted and 7-substituted s-triazolo[2,3-a]pyrimidines were compared. © 1961, The Pharmaceutical Society of Japan. All rights reserved.