The action of alkali on some 9-substituted adenines

Abstract

The action of alkali on some 9-alkyl-adenines has been shown to be of two types: (a) replacement of -NH₂ by -OH, and (b) opening of the imidazole ring to give finally a 4,5-diamino-6-alkylaminopyrimidine. The only compound tested which was stable was 9-carboxymethyladenine; all the other compounds gave some of the corresponding 9-alkyl-hypoxanthine. An approximate correlation between the amount of 4,5-diamino-6-alkylaminopyrimidine and the K_a of the corresponding alkyl-carboxylic acid is given.