[CH3:1][S:2][C:3]1C=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][N:4]=1.[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.[Cl-].[NH4+:17]>O1CCCC1>[CH:11]1([CH:9]([C:6]2[CH:7]=[N:17][C:3]([S:2][CH3:1])=[N:4][CH:5]=2)[OH:10])[CH2:13][CH2:12]1To a solution of 2-(methylthio)pyridine-5-carbaldehyde (2000 mg, 12.97 mmol) in tetrahydrofuran (20 mL) was added a solution of 0.5 mol/L cyclopropylmagnesium bromide in tetrahydrofuran (28.6 mL) at −40° C. under argon atmosphere. The reaction solution was stirred at the same temperature for 10 minutes, and then slowly warmed to 0° C. and stirred for 1 hour. To the reaction solution was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30→60:70) to give cyclopropyl[2-(methylthio)pyrimidin-5-yl]methanol (822 mg, 32%) as a colorless oil.
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