Water → 6-Methoxypyrimidine-4-carbonitrile

To a solution of 4-chloro-6-methoxypyrimidine (10.6 g) in acetonitrile (150 mL) was added 1,4-diazabicyclo[2.2.2]octane (8.18 g), and the mixture was stirred at room temperature for 10 min. Tetraethylammonium cyanide (11.5 g) was added to the obtained reaction mixture, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.00 g) as a pale-yellow oil.