Synthesis of 6-(2-furyl) and 6-(2-thienyl)-4-trifluoromethylpyrimidinones and -pyrimidines from 4-(2-heteroaryl)-4-methoxy-1,1,1-trifluoro-3-buten-2-ones

Abstract

The synthesis of biheterocyclic systems 6-(2-furyl)-pyrimidines and 6-(2-thienyl)-pyrimidines in reasonable yields (50-67%), two 6-(2-heteroaryl)-4-trifluoromethyl-2-(1H)-pyrimidinones (2a,b) and a series of ten 6-(2-heteroaryl)-4-trifluoromethylpyrimidines (3a,b - 7a,b) from the cyclocondensation of 1,1,1-trifluoro-4-(2-heteroaryl)-4-methoxy-3-buten-2-ones with urea and amidines is reported. Structures of all compounds have been elucidated by elemental analysis, mass spectrometry and 1H, 13C NMR measurements. The 1H and 13C NMR data are systematically reported. The X-ray diffraction data for monocrystal from 2-amino-4-trifluoromethyl-6-(thien-2-yl)-pyrimidine (5b) are reported. ©2007 Sociedade Brasileira de Química.