Dimethylformamide → HCID 22401094, compound

HRID 260268Notes

Reaction equation

HRID 260268 reaction equation
CN(C)C=O.[OH:6][C:7]1[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([CH2:12][S:13][CH3:14])[S:10][CH:11]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:6][C:7]2[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([CH2:12][S:13][CH3:14])[S:10][CH:11]=2)[N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 22401105HCID 22401105, compound

Product 1

HCID 22401094HCID 22401094, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of N,N-dimethylformamide was added to 3.5 g (15.1 mmol) of ethyl 4-hydroxy-2-methylthiomethylthiophene-3-carboxylate, 3.3 g (15.1 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 2.1 g (15.2 mmol) of potassium carbonate, and the mixture was heated and stirred at from 90° to 100° C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2.8 g (yield: 50.0%) of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-075aba0d97a548778b56dfc23f4319de
Source dataset
uspto-grants-1996_06
Patent number
US05527763

Reaction notes

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