Water → 1-(2-Amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-ol

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Reaction Steps

A mixture composed of the above 1-(2-amino-4,6-dichloropyrimidin-5-yl)-3-buten-1-ol (57.24 g), N-methylmorpholine-N-oxide (147.6 g), tetrahydrofuran (500 mL), acetone (500 mL), water (500 mL) and osmium tetroxide (62 mg) was stirred at room temperature for two days. After confirming that the raw material disappeared, a saturated sodium thiosulfate solution (1 L) was added, and the reaction mixture was concentrated to about 1.5 L under reduced pressure. The residue was saturated with sodium chloride, followed by extraction with tetrahydrofuran. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure to evaporate the solvent. N,N-Dimethylformamide (500 mL), 2,2-dimethoxypropane (210 mL) and p-toluenesulfonic acid monohydrate (18.61 g) were added to the resulting residue, and the mixture was stirred at room temperature for 14 hours. A saturated sodium bicarbonate solution (1 L) and water (1 L) were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to about 100 mL under reduced pressure. Hexane was added to the residue, followed by stirring. The precipitated crystals were collected by filtration to obtain the title compound (53.88 g, 77%) as a solid.

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