Sodium hydride → 1-Benzyloxycarbonylmethyl-3-(tert-butoxycarbonylmethyl)-2,4-dioxopyrimidine

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Reaction Steps

To a solution of phenylmethyl 2-(2,4-dioxo-1,3-dihydropyrimidinyl)acetate (1.0 g) in anhydrous DMF (10 ml) at 0° C. was added portionwise sodium hydride (0.18 g). After the reaction mixture was stirred for 15 minutes with cooling in an ice bath, tert-butyl bromoacetate (0.9 g) was added. After stirring the mixture at room temperature for 1 hour, to the reaction mixture was added saturated aqueous ammonium chloride solution, and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate 2:1) to give phenylmethyl 2-(3-{[(tert-butyl)oxycarbonyl]methyl}-2,4-dioxo-1,3-dihydropyrimidinyl)acetate (1.2 g) as a colorless oil.

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