2,4-Dimethyl-3-pentanol → 4-(2-Butynyloxy)-6-(1-isopropyl-2-methylpropyloxy)pyrimidine

Participants

Reaction Steps

In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.23 g of 2,4-dimethyl-3-pentanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0.17 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.11 g of sodium hydride (60% in oil), followed by stirring 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 0.44 g of 4-(2-butynyloxy)-6-(1-isopropyl-2-methylpropyloxy)pyrimidine (the present compound (30)).

Provenance & Evidence