3-Methyl-2-butanol → 4-(1,2-Dimethylpropyloxy)-6-(2-pentynyloxy)pyrimidine

Participants

Reaction Steps

In 4 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.24 g of 3-methyl-2-butanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.40 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at 0° C. for 3 hours. To this was added dropwise 0.5 ml of a solution containing 0.29 g of 2-pentyn-1-ol in tetrahydrofuran and further added 0.15 g of sodium hydride (60% in oil), followed by stirring 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 0.44 g of 4-(1,2-dimethylpropyloxy)-6-(2-pentynyloxy)pyrimidine (the present compound (22)).

Provenance & Evidence