To a solution of 2,4,6-trichloropyridine (3.64 g, 20.0 mmol) in DMF (20 mL) was slowly added NaH (60% dispersed in mineral oil, 840 mg, 21 mmol) and methanol (673 mg, 21 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the mixture was concentrated and partitioned between ethyl acetate (30 mL) and water (15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to afford 2,6-dichloro-4-methoxypyridine (3.0 g, yield: 94%) using ethyl acetate (0-5%) in hexane as eluent.
