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

Beteiligte Stoffe

Reaktionsschritte

In 2 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.10 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 4,5,6-trichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 6 hours. To this was added dropwise 0.3 ml of a solution containing 0.08 g of 2-butyn-1-ol in tetrahydrofuran and further added 0.05 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 0.15 g of 4-(2-butynyloxy)-5-chloro-6-(1,2-dimethylpropyloxy)pyrimidine (the present compound (24)).

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