Potassium Carbonate → 4-(Pyrimidin-5-yloxy)benzaldehyde

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To a solution of pyrimidin-5-ol (500 mg, 5.20 mmol) in DMF (5.20 mL) under argon was added 4-fluorobenzaldehyde (0.558 mL, 5.20 mmol), sodium methanesulfinate (133 mg, 1.30 mmol), and potassium carbonate (1.079 g, 7.81 mmol). The reaction mixture was heated at 120° C. for 3 hour. The mixture was allowed to cool to room temperature and was diluted with water (25 mL). The mixture was extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine (2×50 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate], providing 4-(pyrimidin-5-yloxy)benzaldehyde (666 mg) as a yellow solid. LCMS m/z 201.0 (M+H)+, Rt 0.52 min.

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