Cesium fluoride → 4-Chloro-6-phenylpyrimidine

Participants

Reaction Conditions

Reaction Steps

Phenylboronic acid (3.05 g, 25 mmol) was added to a solution of 4,6-dichloropyrimidine (7.45 g, 50 mmol) in 50 mL of dimethoxyethane at 70° C. followed by cesium fluoride (7.60 g, 50.0 mmol). The resulting mixture was stirred for 5 minutes at 80° C. and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.04 g, 2.5 mmol) was then added. The reaction mixture was stirred at 80° C. for one hour then evaporated. The residue was extract with ether (3×50 mL) and EtOAc (1×50 mL). The combined organic layers were washed with 100 mL saturated sodium carbonate solution (100 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography (Biotage 40 L eluting with 250 mL each of 0, 10, 20, 30, 40, 50, 60, 70, 80, and 100% dichloromethane/petroleum ether) to afford 2.20 g, (46.2%) of the product. MS 191.0 (AP+, 100).

Provenance & Evidence