Water → HCID 67818640, compound

HRID 593199Notes

Reaction equation

HRID 593199 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:20]([CH3:30])([CH3:29])[C:21]([C:23]1[CH:24]=[N:25][CH:26]=[N:27][CH:28]=1)=[O:22].O>CS(C)=O>[CH3:29][C:20]([O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1)([CH3:30])[C:21]([C:23]1[CH:28]=[N:27][CH:26]=[N:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 67814920HCID 67814920, compound

Product 1

HCID 67818640HCID 67818640, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4.4 g (25.0 mmol) of 4-trifluoromethoxyphenol and 15.5 g (112.5 mmol) of potassium carbonate in 37.5 ml of dry dimethyl sulphoxide was stirred at room temperature for 2 h. The reaction mixture was subsequently warmed to 60° C., and 25.7 g (112.5 mmol) of 2-bromo-2-methyl-1-(pyrimidin-5-yl)propan-1-one, dissolved in 12.5 ml of dimethyl sulphoxide, were added. After the addition had ended, the reaction mixture was stirred overnight. The reaction mixture was poured into 250 ml of water and extracted with 250 ml of ethyl acetate. The organic phase was separated off and then washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The crude product was then purified by column chromatography. This gave 1.24 g (14%) of the desired product.

Workup

  1. temperatureThe reaction mixture was subsequently warmed to 60° C.
  2. additionwere added
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred overnight
  5. extractionextracted with 250 ml of ethyl acetate
  6. customThe organic phase was separated off
  7. washwashed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-bea4985dc2554685b9d77f0dbdbb1af5
Source dataset
uspto-grants-2016_01
Patent number
US09241487B2

Reaction notes

Loading…