Water → 5-Iodo-1,3-diethyl-6-methyl uracil
Reaction equation
[I:1][C:2]1[C:3](=O)[NH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH2:17](I)[CH3:18].O.[CH3:21]N(C=O)C>C(OCC)(=O)C>[I:1][C:2]1[C:11](=[O:14])[N:6]([CH2:7][CH3:8])[C:5](=[O:9])[N:4]([CH2:17][CH3:18])[C:3]=1[CH3:21]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 5-iodo-6-methyl uracil (20.97 mmol, 5.45 g) and powdered potassium carbonate (60 mmol, 8.29 g) in DMF (188 mL) was added ethyl iodide (83.88 mmol, 6.7 mL). The reaction mixture was stirred for 15 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 were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration gave a crude solid which was triturated with dichloromethane/diethyl ether/hexanes (1:1:1) to afford 3.89 g (60% yield) of 5-iodo-1,3-diethyl-6-methyl uracil as a white crystalline solid: mp 159-161.5° C. EI-HRMS m/e calcd for C9H13IN2O2 (M+) 308.0022, found 308.0018.
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
- washThe combined extracts were washed with brine solution (150 mL)
- dry with materialwere dried over anhydrous magnesium sulfate
- filtrationFiltration of the drying agent and concentration
- customgave a crude solid which
- customwas triturated with dichloromethane/diethyl ether/hexanes (1:1:1)
Sources & evidence
- ORD record
- ord-fa7a37135efa4b3fa09b279c5326e2af
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380387B1
Reaction notes
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