Green chemical principles based regioselective functionalization of 2,4,6-trichloropyrimidine-5-carbaldehyde: Application in the synthesis of new pyrimidines and pyrrolopyrimidine

Abstract

The present work reports the synthesis of three new nitrogen-containing heteronuclear molecules (two pyrimidines and one pyrrolopyrimidine). Based on the 12 principles of green chemistry, chemical methodologies are planned and executed. Various phase transfer catalysts were examined in the crucial step to execute C–N bond formation (through the SnAr mechanism), TBAI was found to be a better option than those of TBAB and CTAB. The one-pot synthetic methodology was optimized involving Wittig olefination and bromination to achieve a key precursor for the synthesis of a new pyrrolopyrimidine.

Keywords

• twelve principles of green chemistry
• phase transfer catalysis
• one-pot synthesis
• wittig olefination
• synthesis of new n-heterocyclic compounds
• halogen solvent-free processes
• catalytic reactions