Sodium hydride → HCID 17979099, compound

Participants

Reaction Steps

In 3 ml of tetrahydrofuran was suspended 0.17 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.17 g of 2-pentyn-1-ol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of tetrahydrofuran containing 0.37 g of 3-(6-chloro-4-pyrimidyloxy)-2-methyl-2-butanol dissolved therein, followed by stirring at the same temperature for 1 hour and at room 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 0.33 g of 4-(2-pentynyloxy)-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine.

Provenance & Evidence