Under an argon atmosphere, to a solution of (6-(2-fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methanol (587 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (587 mg) in THF (9.6 mL) was added 60% sodium hydride (100 mg) at 0° C., and the mixture was stirred at room temperature for 4 hr. 1N Hydrochloric acid was added to the reaction mixture at 0° C., and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (890 mg) as a colorless oil.
