To a solution of 4,6-dichloropyrimidine (1.0 g, 6.71 mmol) in tetrahydrofuran (30 mL) was added sequentially 1-methyl-2-pyrrolidinone (3.2 mL, 6.71 mmol), iron(III) acetylacetonate (0.119 g, 0.336 mmol) and methylmagnesium bromide (2.237 mL, 6.71 mmol). The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate (100 mL). The organic layer was separated and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane) to afford 4-chloro-6-methylpyrimidine (0.6 g, 3.08 mmol, 46% yield) as a colorless gelatinous liquid.LC-MS (ESI) analysis showed m/z 129.0 [M+H]+ (calculated value C5H6ClN2: 129.0); LC/MS retention time ( Method D): 1.36 min.
