2,4,5-Trichloropyrimidine → 2,5-Dichloro-4-methylpyrimidine

Participants

Reaction Conditions

Reaction Steps

2,4,5-Trichloropyrimidine (250 mg, 1.36 mmol) and ferric acetylacetonate (24 mg, 0.07 mmol) were taken up in tetrahydrofuran (2.7 ml) and the reaction was cooled to −78° C. Methylmagnesium bromide (0.45 ml of 3 M in THF, 1.36 mmol) was added dropwise and the mixture was stirred at −78° C. for one hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by Combiflash (0-10% diethylether in hexanes) to provide 2,5-dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45%) as a white solid. MS APCI: [M+H]+ m/z 163.0.

Provenance & Evidence