Example 9: Synthesis of 2-chloro-5-(phenylmethoxy)pyrimidine (compound 31)
Under the guidance of the reference reaction scheme, potassium carbonate (11.6 g, 84.3 mmol) was added to a 500 mL methanol solution containing 10 g of 2-chloro-5-hydroxypyrimidine (76.6 mmol), followed by benzyl bromide (10.1 mL, 84.3 mmol). The reaction mixture was stirred at room temperature for 14 hours. Upon completion of the reaction, water (300 mL) was added to terminate the reaction. Methanol was removed by evaporation and the remaining aqueous layer was extracted with chloroform. The combined chloroform layers were washed with brine, dried with anhydrous magnesium sulfate and filtered. After removal of the solvent, the product was purified by silica gel column chromatography using 100:1 chloroform:methanol as eluent to afford 15 g (89% yield) of 2-chloro-5-(phenylmethoxy)pyrimidine (31) as a white solid.
1H NMR (CDCl3) δ 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).
