Water → HCID 12802681, compound

Participants

Reaction Conditions

Reaction Steps

A solution of α-acetoxymethoxybenzyl alcohol acetate (1.43 g; 6 mmoles) prepared in Example I - 1 and 2,4-di-(trimethylsilyloxy)-5-fluoropyrimidine (1.37 g; 5 mmoles) in dry acetonitrile (25 ml) is cooled at 0° C. Stannic chloride (d=2.26; 0.58 ml; 5 mmoles) is added thereto, and the mixture is stirred at 0° C. for 30 minutes, then mixed with sodium hydrogencarbonate (2.52 g; 30 mmoles) and water (2.5 ml), and vigorously stirred at 0° C. The insoluble materials are filtered off and washed with acetonitrile and methylene chloride. The organic layer is washed with an aqueous saturated solution of sodium hydrogencarbonate and then with saturated brine, dried over magnesium sulfate, and evaporated. The residue is chromatographed on a column of silica gel and eluted with benzene-ethyl acetate (2:1). The eluate is recrystallized from ether to give the title compound (0.88 g; yield 57%). mp. 108°-109° C.

Provenance & Evidence