3-Fluorophenylboronic acid → Ethyl 2-tert-butyl-4-(3-fluorophenyl)pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

In a mix of sat'd NaHCO3:toluene:ethanol (1:2:1) (8 mL) was dissolved ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate from Example B40 (300 mg, 1.24 mmol), 3-fluorophenylboronic acid (350 mg, 2.47 mmol) and to this was added tetrakis(triphenylphosphine)palladium(0) (29 mg). The mixture was heated overnight at 75° C. under Ar. The mixture was diluted with EtOAc (25 mL) and water (25 mL). The mixture was filtered to remove insolubles and the organic phase separated, washed with 5% citric acid (25 mL), then saturated sodium bicarbonate (25 mL) and brine (25 mL). The solvents evaporated at reduced pressure and the residue purified by silica gel column chromatography (Biotage: 25M, 5-50% EtOAc/Hex—550 mL) to give ethyl 2-tert-butyl-4-(3-fluorophenyl)pyrimidine-5-carboxylate (0.27 g, 72% yield).

Provenance & Evidence