Water → HCID 15477229, compound

HRID 366329Notes

Reaction equation

HRID 366329 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])=[C:11]([F:26])[CH:10]=[C:9]([Cl:27])[C:7]=2[CH:8]=1)([OH:3])=[O:2].[C:28](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:27][C:9]1[C:7]2[CH:8]=[C:4]([C:1]([O:3][CH3:28])=[O:2])[O:5][C:6]=2[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[N:15]([CH3:24])[C:14]2=[O:25])=[C:11]([F:26])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15477227HCID 15477227, compound

Product 1

HCID 15477229HCID 15477229, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.21 g (0.5 mmol) of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.16 g (1.1 mmol) of potassium carbonate were suspended in 10 ml of N,N-dimethylformamide, and 0.15 g (1.1 mmol) of methyl iodide was added thereto at room temperature, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.21 g (yield: 96.8%) of the desired product as yellowish brown crystals. Melting point: 194-196° C.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cded38d61d264d1d9ed4d6af8ec9fca4
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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