Methyl iodide → 3-(4-Bromo-5-ethoxy-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1h,3h)-pyrimidinedione

HRID 566182Notes

Reaction equation

HRID 566182 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]2=[O:22])=[C:4]([F:23])[CH:3]=1.CI.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:26])[C:12]2=[O:22])=[C:4]([F:23])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 212655333-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 110801123-(4-Bromo-5-ethoxy-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1h,3h)-pyrimidinedioneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (2.38 g), methyl iodide (1.06 g) and potassium carbonate (1.04 g) were suspended in DMF (12 ml), and the mixture was stirred at room temperature for about 8 hours. After the reaction, DMF was distilled off under reduced pressure, extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off, and the resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:5 v/v) to obtain the objective 3-(4-bromo-5-ethoxy-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4( 1H,3H)-pyrimidinedione (2.08 g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, ethyl acetate was distilled off
  6. customthe resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:5 v/v)

Sources & evidence

ORD record
ord-ef6aaa9530ca4b3a8a382ef03a20afbf
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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