2-Butyn-1-ol → HCID 17979102, compound

Participants

Reaction Steps

In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.05 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 0.3 ml of a solution containing 0.16 g of 4-chloro-6-(2,2-dimethoxy-1-methylethoxy)pyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 1 hour and further 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 0.11 g of 4-(2-butynyloxy)-6-(2,2-dimethoxy-1-methylethoxy)pyrimidine (the present compound (18)).

Provenance & Evidence