Synthesis of 5-stannylpyrimidines and their use in Pd-catalysed ketone formation

Abstract

2-(Dimethyl-t-butylsiloxy)-5-stannylpyrimidines have been prepared from the lithiated pyrimidine precursor. 2-Methylthio-5-stannylpyrimidines were prepared similarly and oxidized chemoselectively to the corresponding sulphones. 5-Stannylpyrimidin-2(1H)-ones can be prepared by fluoride-induced removal of the silyl group in 2-(dimethyl-t-butylsiloxy)-5-stannylpyrimidines, and the 5-stannylated pyrimidinones can be N-alkylated. The stannylated pyrimidines are stable compounds which react readily with acid chlorides in Pd-catalysed reactions with formation of 5-pyrimidinyl ketones.