Improved Synthesis and Efficient Chemoselective Reduction of Fused Tetrazoles under Phase-Transfer Conditions

Abstract

Liquid-liquid phase-transfer conditions were employed in an improved synthesis of 7,9-substituted 7H-pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidines and 5,7-substituted 4-amino-7H-pyrrolo[2,3-d]pyrimidines. The latter were obtained either by reductive ring cleavage of the former, or by one-pot synthesis from 5,7-substituted 4-chloro-7H-pyrrolo[2,3-d]pyrimidines.

Key words

pyrrolotetrazolopyrimidines - reductive ring cleavage - phase-transfer catalyst - Aliquat 336 - 18-crown-6

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