Synthesis
1. 5-Bromo-4-chloro-6-methylpyrimidine (1.85 g, 8.92 mmol) was dissolved in 50 mL of methanol, and a methanolic solution of 25 wt% sodium methanolate (1.83 mL, 16.0 mmol) was added with stirring. 2. The reaction mixture was stirred for 1 hr at room temperature. 3. Upon completion of the reaction, the reaction was quenched by addition of a buffer solution of pH 7. 4. A large portion of the methanol was removed by reduced pressure distillation. Most of the methanol was removed by distillation under reduced pressure. 5. The remaining aqueous phase was diluted with water and extracted three times with ether. 6. The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 5-bromo-4-methoxy-6-methylpyrimidine (1.43 g, 79% yield). 7. The product was confirmed by 1H NMR (CDCl3, 400 MHz) and mass spectrometry (ES): 1H NMR δ 8.48 (s, 1H), 4.00 (s, 1H), 4.00 (s, 1H), and 4.00 (s). 1H), 4.00 (s, 3H), 2.54 (s, 3H); MS (ES) m/z 204 [M + 1]+.
