Methyl iodide → HCID 21265544, compound

HRID 566188Notes

Reaction equation

HRID 566188 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[NH:10][C:9]2=[O:20])=[C:4]([F:21])[CH:3]=1.CI.[C:24](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([C:16]([F:19])([F:17])[F:18])[N:10]([CH3:24])[C:9]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21265538HCID 21265538, compound

Product 1

HCID 21265544HCID 21265544, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(4-Bromo-2-fluorophenyl)-5-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (16.52 g), methyl iodide (7.99 g) and potassium carbonate (7.76 g) were suspended in DMF (90 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. Ethyl acetate was distilled off, and the resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v) to obtain the objective 3-(4-bromo-2-fluoro-phenyl)-1,5-dimethyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (14.92 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. distillationEthyl acetate was distilled off
  6. customthe resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v)

Sources & evidence

ORD record
ord-49a6570ffaa64e7fb0f40c6aa587fd97
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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