Purines. V. Reaction of 9-phenyl-9H-purine-6-carbonitrile with nucleophilic reagents.

Abstract

The reaction of 9-phenyl-9H-purine-6-carbonitrile (1) with nucleophilic reagents occurred by addition of the reagent across the C-N triple bond of the cyano group, and substitution of the cyano group was not observed. Thus, the reactions with hydroxylamine, hydrazine, amines, Grignard reagents, and 98% sulfuric acid gave the corresponding amidoxime (2), amidorazone (3), amidines (4), ketones (5), and amide (7), respectively. Alcoholysis of 1 gave the ester (6) and 7 together with the ring fission product of the imidazole portion, alkyl 5-amino-6-anilino-4-pyrimidine-carboxylate (8). Amides (10), the hydroxamic acid (11), and the hydrazide (12) were prepared from the methyl ester (6a).