67434-65-5

4316-97-6

13061-96-6

67434-65-5

GENERAL STEPS: 4,6-Dichloro-5-methylpyrimidine (Sigma-Aldrich, item 595446, 0.50 g, 3.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol) were dissolved in toluene (6 mL). Cesium carbonate (3 g, 9.20 mmol) was added to the mixture, followed by methylboronic acid (0.20 g, 3.37 mmol) and N,N-dimethylformamide (DMF, 1 mL). The reaction mixture was placed in a microwave reactor and heated by microwave radiation at 140°C (2 cycles of 30 min each). Upon completion of the reaction, it was cooled to room temperature and filtered. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (EtOAc) and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and brine. The organic phase was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to afford the target product 4-chloro-5,6-dimethylpyrimidine (0.18 g, 1.26 mmol, 41% yield). The product was analyzed by ultra-performance liquid chromatography (UPLC) with a retention time (rt) of 0.53 min, and the major peaks observed were 143 ([M + 1-HCl], 100%) and 445 ([M + 1-HCl], 33%). The elemental analysis results were consistent with the theoretical calculated value (142) for C6H7ClN2.1H NMR (400 MHz, CDCl3) δ (ppm): 8.70 (s, 1H), 2.57 (s, 3H), 2.39 (s, 3H).