Water → 5-Iodo-1,3-dimethyluracil

A mixture of 5-iodo uracil (22.2 mmol, 5.28 g) and powdered potassium carbonate (60 mmol, 10.3 g) in DMF (188 mL) was stirred for 24 h at room temperature and then methyl iodide (53.5 mmol, 3.33 mL) was added. Then, the reaction mixture was stirred for another 72 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 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 mixture (3:1, 120 mL), water (30 mL), hexane (30 mL) and dried under vacuum to obtain 4.61 g (78%) of 1,3-dimethyl 5-iodo uracil as white needles (mp 226-228° C., Lit. 225-227° C., Synthetic communication 1988, 18, 855-867). EI-HRMS m/e calcd for C6H7IN2O2 (M+) 266.0021, found 266.0023.

1. stirringThen, the reaction mixture was stirred for another 72 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
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
12. dry with materialwater mixture (3:1, 120 mL), water (30 mL), hexane (30 mL) and dried under vacuum

ORDレコード

ord-9e5a0f05272d4207b87ac4e5dde354aa

出典データセット

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06380387B1