Potassium Phosphate, Tribasic → 2-Chloro-4-[(1E)-3-methoxy-1-propen-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A microwave vessel was charged with 2,4-dichloropyrimidine (500 mg, 3.36 mmol), 3-acetoxy-1-propenylboronic acid pinacol ester (997 mg, 5.03 mmol) and solid potassium phosphate tribasic (2.14 g, 10.1 mmol), which were then suspended in 2-methyltetrahydrofuran (4 ml) and water (1 ml). The vessel was deoxygenated three times, then Palladium(II) acetate (37.7 mg, 0.17 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (138 mg, 0.34 mmol) were introduced and the dark mixture was heated under microwave irradiation at 125° C. for 15 min. The reaction mixture was diluted with saturated aqueous NaHCO3 (80 ml) and extracted with EtOAc (2×75 ml). The combined organic layers were dried over MgSO4 and concentrated. The crude orange oil was purified by flash column chromatography (SiO2: 100% Hex to 100% EtOAc), which afforded 2-chloro-4-[(1E)-3-methoxyprop-1-en-1-yl]pyrimidine (623 mg, 3.21 mmol, 96% yield) as an orange-red solid. MS ESI: [M+H]+ m/z 185.1.

Provenance & Evidence