3-Methyl-2-butanol → 4-(2-Butynyloxy)-6-(1,2-dimethylpropyloxy)-5-methylpyrimidine

Participants

Reaction Steps

In 2 ml of tetrahydrofuran was suspended 0.06 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.11 g of 3-methyl-2-butanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.20 g of 4,6-dichloro-5-methylpyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 5 hours. To this was added dropwise 0.3 ml of a solution containing 0.10 g of 2-butyn-1-ol in tetrahydrofuran and further added 0.06 g of sodium hydride (60% in oil), followed by 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 0.20 g of 4-(2-butynyloxy)-6-(1,2-dimethylpropyloxy)-5-methylpyrimidine (the present compound (25)).

Provenance & Evidence