2,4-Dichloropyrimidine → 4-(2-thienyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a degassed 0.50 M solution of 2,4-dichloropyrimidine (1.0 eq.) and 5-(1,3-dioxolan-2-yl)-2-thienylzinc bromide 31 (1.0 eq.) in tetrahydrofuran was added tetrakis(triphenylphosphine)palladium(0) (0.050 eq.). The mixture was stirred for 16 h at 70° C. and then returned to ambient temperature and diluted with ether. The solution was washed sequentially with a 0.5 M aqueous pH 9 solution of EDTA and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography over silica gel (1:1:1 hexanes:ethyl acetate:dichloromethane) to give compound 32. ES/MS m/z 269 (MH+), C11H9ClN2O2S=269 g/mol.

Provenance & Evidence