31458-33-0

4595-59-9

289-95-2

31458-33-0

General procedure for the synthesis of 5-methoxypyrimidine from 5-bromopyrimidine: A 170 mL methanol solution of 15 g (0.094 mol) 5-bromopyrimidine and 5.4 g (0.10 mol) sodium methanol was added to an autoclave. The mixture was heated and reacted at 100-120°C for 16 hours. After completion of the reaction, the dark brown mixture was neutralized with glacial acetic acid and subsequently extracted three times with ether. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting brown solid was purified by silica gel column chromatography employing a 9:1 ethyl acetate/hexane solvent mixture as eluent to afford light yellow crystals of 5-methoxypyrimidine (7 g, 70% yield). Alternatively, the product can be purified by distillation under reduced pressure with a boiling point of 76 °C (10 mmHg).