3-Dimethylamino-3'-trifluoromethylacrylophenone → Phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]-pyrimidin-3-yl]methanon

HRID 231500Notes

Reaction equation

HRID 231500 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][NH:4][N:3]=1.CN(C)[CH:17]=[CH:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)=O>C(O)(=O)C>[C:9]1([C:7]([C:6]2[CH:5]=[N:4][N:3]3[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)=[CH:18][CH:17]=[N:1][C:2]=23)=[O:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenoneHCID 178509267HCID 178509267, compound

Product 1

HCID 13475887Phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]-pyrimidin-3-yl]methanon

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture of 1.87 g of (3-amino-1H-pyrazol-4-yl)phenyl-methanone and 2.43 g of 3-dimethylamino-1-[3-(trifluoromethyl)phenyl]-2-propen-1-one in 25 ml of glacial acetic acid was refluxed for 6 hours and then the solvent was removed in vacuo giving a crystalline residue. This residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was dried with anhydrous sodium sulfate and then passed through a short pad of hydrous magnesium silicate. The addition of hexane to the refluxing eluate induced crystallization. After cooling, the desired product was collected as crystals, mp 148°-150° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customthe solvent was removed in vacuo
  3. customgiving a crystalline residue
  4. customThis residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. additionThe addition of hexane
  7. customto the refluxing eluate induced crystallization
  8. temperatureAfter cooling
  9. customthe desired product was collected as crystals, mp 148°-150° C.

Sources & evidence

ORD record
ord-a71a969994fc4bdfa078a0a0fba898a7
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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