Potassium Phosphate, Tribasic → 2-Chloro-5-cyclopropylpyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-chloropyrimidine (100 mg, 0.517 mmol, Aldrich), cyclopropylboronic acid (57.7 mg, 0.672 mmol, Aldrich), Tricyclohexylphosphine (14.50 mg, 0.052 mmol, Aldrich) and K3PO4 (384 mg, 1.81 mmol, EMD) in Toluene (2 mL) and Water (0.110 mL) was degassed by vacuum and purged with Ar. To the resulting mixture was added Palladium(II) acetate (5.80 mg, 0.026 mmol, Stem) and then heated under microwave conditions at 120° C. for 10 min. The reaction mixture was quenched with H2O and then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0 to 20% EtOAc in Hexanes) to yield 71 mg of the desired compound as a white solid. MS (ESI) 155 (M+H).

Provenance & Evidence