Cesium carbonate → 4-[2-(5-Chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidine (320 mg, 1.13 mmol, 1 eq) in dioxane (5 ml) was added Pd(OAc)2 (13 mg, 0.06 mmol, 0.05 eq) followed by BINAP (53 mg, 0.08 mmol, 0.075 eq), 4-aminonicotinic acid ethyl ester (206 mg, 1.24 mmol, 1.1 eq) and Cs2CO3 (478 mg, 1.46 mmol, 1.5 eq). The reaction mixture was heated to 80° C. for 15 h. The reaction mixture was cooled to rt and filtered through Celite® and the crude material was purified by flash column chromatography (0-5%MeOH in CHCl3) to afford 4-[2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid ethyl ester (100 mg, 21%) as a white solid.

Provenance & Evidence