Pyrrolopyrimidine nucleosides. Part XI. Influence of amino-groups at C-4 and C-6 or an amino-group at C-6 on the reactivity of a 5-cyano-group in pyrrolo[2,3-d]pyrimidine nucleosides

Abstract

The syntheses of 6-amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (7) and its 4,6-diamino-analogue (12) are described. Nucleophilic addition to the 5-cyano-group of both (7) and (12) was found to be more difficult under both acidic and basic conditions than addition to the nitrile group of toyocamycin (3) or 7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (1). The reaction of hydrazine with 6-bromo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile, which furnished a tricyclic nucleoside, is discussed.