Trifluoromethyluracil → 1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a suspension of 50% NaH (0.42 g, 8.7 mmol) in DMF (5 mL), a solution of 5-trifluoromethyl-1H-pyrimidine-2,4-dione (1.2 g, 6.66 mmol) was added drop wise maintaining the temperature at 0° C. The mixture was then heated at 100° C. for 1 hour. After cooling to room temperature, (3-bromo-propoxy)-tert-butyl-dimethyl-silane (2 mL, 8.7 mmol) was added and the reaction was stirred overnight. The solvent was evaporated and the crude was dissolved in a 25%aq solution of citric acid and extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give 0.87 g of 1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione (37% yield).

Provenance & Evidence