Synthesis of 2,6-Substituted 7-(Het)aryl-7-deazapurine Nucleobases (2,4-Disubstituted 5-(Het)aryl-pyrrolo[2,3-d]pyrimidines)

Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

A series of 7-(het)aryl-7-deazapurine nucleobases (5-[(het)aryl]-2,4-disubstituted 7H-pyrrolo[2,3-d]pyrimidines) bearing NH₂, OMe, SMe, or Me groups at position 6 and H, NH₂, or Me at position 2 were prepared by the aqueous Suzuki–Miyaura cross-coupling reactions from SEM-protected 7-iodo-7-deazapurines with (het)arylboronic acids followed by deprotection. The 6-methoxy derivatives were further transformed into 7-deazahypoxanthines or 7-deazaguanines by O-demethylation reactions. Unlike their ribonucleoside counterparts, the 7-deazapurine nucleobases did not exert any significant cytostatic or antiviral effects.

Key words

deazapurines - pyrrolo[2,3-d]pyrimidines - nucleobases - Suzuki­–Miyaura cross-coupling - deprotection - demethylation

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