反应详情

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.

1. stirringThe reaction mixture was stirred for another 76 h at room temperature
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
4. washThe combined extracts were washed with brine solution (150 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationFiltration of the drying agent and concentration of the solvent
7. customgave crude solid which
8. customwas crystallized from ethanol:water (3:1, 150:50 mL)
9. customstored in the refrigerator overnight
10. filtrationThe solids were collected by filtration
11. washwashed with ethanol:water (3:1, 120 mL), water (30 mL), hexanes (30 ML)
12. customdried under high vacuum