Dimethylformamide → HCID 15070268, compound

HRID 1534085Notes

Reaction equation

HRID 1534085 reaction equation
C([C:3]([OH:16])([C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[C:4](O)=[O:5])C.[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.[C:31](=O)([O-])[O-].[K+].[K+].CN(C)[CH:39]=[O:40]>>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([O:16][CH:3]([C:7]([CH3:8])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:15])[C:4]([O:40][CH2:39][CH3:31])=[O:5])[N:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19910246HCID 19910246, compound

Product 1

HCID 15070268HCID 15070268, compound

Conditions

Temperature
100 °C

Procedure

4.5 g of ethyl 2-hydroxy-3-methyl-3-phenylbutyric acid, 4,6 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine, 5,3 g of anhydrous potassium carbonate and 50 ml of N,N-dimethylformamide were introduced to a round bottom flask, and the mixture was stirred at 100° C. for 3 hours. Then, the reaction mixture was poured into ice water and extracted twice with 50 ml of ethyl acetate. The extract was washed with water and then dried over anhydrous sodium sulfate overnight. An inorganic salt was removed by filtration, and then the solvent was distilled off under reduced pressure to obtain 7 g of crude crystals. The crude crystals were recrystallized from ethanol to obtain 5.6 g of the desired product.

Workup

  1. extractionextracted twice with 50 ml of ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate overnight
  4. customAn inorganic salt was removed by filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain 7 g of crude crystals
  7. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-98aec370201447f8a8c464f163f7c93d
Source dataset
uspto-grants-1992_02
Patent number
US05087289

Reaction notes

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