N. E. Britikova, K. Y. Novitskii, L. I. Shcherbakova
Dec 1, 1977
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Journal
Pharmaceutical Chemistry Journal
Abstract
Earlier we reported the preparation of the previously unknown 2-methyl-4-oxo-3,4-dihydropyrrolo[3,2-d]pyrimidine-7-aldehyde, and from it the nitrile (I) and the pyrrolo[3,2-d]pyrimidine unsubstituted at position 7 (II). Nitrile I and pyrrolopyrimidine II were used in the present work for the preparation of pyrrolo[3,2-d]pyrimidines containing, as substituents in position 4, amino groups (Va-e and Via-d) or sulfhydryl (Vf and Vie). To prepare these compounds, 4-oxopyrrolo[3,2-d]pyrimidines I and II were treated with phosphorus oxychloride, and the 4-chloro derivatives (III and IV) thus obtained, were treated with nucleophilic reagents, such as amines or sodium hydrosulfide. It was observed that the presence of the nitrile group in the 7 position increased the reactivity of the chlorine, compared to the pyrrolopyrimidine unsubstituted at the 7 position. The chloroderivative III reacts with amines in boiling ethanol to form the amino derivatives Va-c. III reacts with aniline hydrochloride or withglycine methyl ester in water to form Vd or Ve. Under analogous conditions the chlorine atom in compound IV is not replaced by an amine residue. The reaction proceeds only in boiling butanol.