Water → 1-((benzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

After N,O-bis(trimethylsilyl)acetoamide (18.5 ml, 74.8 mmol) was added dropwise to a suspension of pyrimidine-2,4-dione (3.36 g, 30.0 mmol) in dichloromethane (90 ml) at room temperature, the mixture was stirred for 2 hours. Tetra-n-butyl ammonium iodide (1.12 g, 3.0 mmol) was added to the reaction mixture, and benzyloxymethyl chloride (4.4 ml, 31.7 mmol) was further added to it. This mixture was stirred at room temperature for 3 hours. The reaction mixture was neutralized with water and a saturated aqueous solution of sodium hydrogencarbonate, and it was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous solution of sodium thiosulfate and with water successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The solid residue was washed with diisopropyl ether and collected by filtration to give the title compound (6.00 g, yield 86%) as a white powder.

Provenance & Evidence