Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:11][CH:12]([Cl:16])[CH:13]([OH:15])[CH3:14].[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[Cl-].[NH4+]>O1CCCC1>[CH2:17]([O:21][C:2]1[CH:7]=[C:6]([O:15][CH:13]([CH3:14])[CH:12]([Cl:16])[Cl:11])[N:5]=[CH:4][N:3]=1)[C:18]#[C:19][CH3:20]
First, 0.38 g of 4,6-dichloropyrimidine was dissolved in 5 ml of tetrahydrofuran, to which 0.12 g of sodium hydride (60% in oil) was added and 0.4 ml of a solution containing 0.33 g of 1,1-dichloro-2-propanol in tetrahydrofuran was added dropwise at 0° C., followed by stirring at 0° C. for 2 hours. To this was added dropwise 0.4 ml of a solution containing 0.16 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.10 g of sodium hydride (60% in oil), followed by stirring at room temperature for 3 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 0.32 g of 4-(2-butynyloxy)-6-(2,2-dichloro-1-methylethyloxy)pyrimidine (the present compound (29)).
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