Phenol → Ethyl 2-phenoxypyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-chloropyrimidine-5-carboxylate (0.5 g, 2.7 mmol) in N,N-dimethylformamide (6.0 mL) was added cesium carbonate (676 mg, 2.1 mmol) and phenol (205 mg, 2.18 mmol). The mixture was stirred at 100° C. for 24 hours. The mixture was concentrated in vacuo. To the residue, was added water (50 mL) and extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulphate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20/1) to give the product ethyl 2-phenoxypyrimidine-5-carboxylate (472 mg, 81%) as colorless oil. 1H NMR (300 MHz, CDCl3): δ 8.55 (s, 2H), 7.43-7.06 (m, 5H), 4.29 (q, J=8.9 Hz, 2H), 1.31 (t, J=8.9 Hz, 3H).

Provenance & Evidence