Trifluoromethyluracil → 1-Ethyl-5-trifluoromethyl uracil

HRID 2194750Notes

Reaction equation

HRID 2194750 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([N:7]1[CH:8]=[C:3]([C:2]([F:11])([F:1])[F:12])[C:4](=[O:10])[NH:5][C:6]1=[O:9])[CH3:21]

Participants

5

Reactant 3

HCID 5899TrifluoromethyluracilHCID 6340IodoethaneHCID 11430Potassium Carbonate

Product 1

HCID 207318431-Ethyl-5-trifluoromethyl uracilYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5-trifluoromethyl uracil (1.8 g, 10 mmol) and powdered anhydrous potassium carbonate (1.38 g, 10 mmol) in DMF (50 mL), was added iodoethane (0.8 mL, 10 mmol). After stirring overnight at room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent ethyl acetate:hexane (1:1)) to afford 563 mg (27%) of 1-ethyl-5-trifluoromethyl uracil as a white solid. m.p. 259-260° C.; 1H-NMR (200 MHz, CDCl3/CD3OD) δ 1.35 (3H, d, J=7.2 Hz), 3.87 (2H, q, J=7.2 Hz), 7.94 (1H, s); m/z (EI) 208 (M+).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-519ecb48f65c45dd95334ef22ccc5221
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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