2-Butyn-1-ol → 4-(2-Butynyloxy)-6-(3-chloro-2,2-dimethylpropyloxy)pyrimidine

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Reaction Steps

In 5 ml of tetrahydrofuran was suspended 0.14 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.22 g of 2-butyn-1-ol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.62 g of 4-chloro-6-(3-chloro-2,2-dimethylpropyloxy)pyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 4 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-(2-butynyloxy)-6-(3-chloro-2,2-dimethylpropyloxy)pyrimidine (the present compound (10)).

Provenance & Evidence