Water → 5-Iodo-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

A mixture of 5-iodo-6-methyl uracil (22.18 mmol, 5.58 g) and powdered potassium carbonate (60 mmol, 8.29 g) in DMF (188 mL) was stirred for 24 h at room temperature and then methyl iodide (90.6 mmol, 3.33 mL) was added. The reaction mixture was stirred for another 76 h at room temperature and was poured into water (150 mL) and ethyl acetate (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine solution (150 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent gave crude solid which was crystallized from ethanol:water (3:1, 150:50 mL) and stored in the refrigerator overnight. The solids were collected by filtration and washed with ethanol:water (3:1, 120 mL), water (30 mL), hexanes (30 ML) and dried under high vacuum to obtain 5.8 g (93% yield) of 5-iodo-1,3,6-trimethyl uracil as a white solid: mp 155-157° C. EI-HRMS m/e calcd for C7H9IN2O2 (M+) 279.9709, found 279.9709.

Provenance & Evidence