[H-].[Na+].[Cl:3][CH2:4][C:5]([CH3:9])([CH3:8])[CH2:6][OH:7].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:10][C:11]1[CH:16]=[C:15]([O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][Cl:3])[N:14]=[CH:13][N:12]=1In 5 ml of tetrahydrofuran was suspended 0.14 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.36 g of 3-chloro-2,2-dimethyl-1-propanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.4 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.62 g of 4-chloro-6-(3-chloro-2,2-dimethylpropyloxy)pyrimidine.
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