4,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione → 5-Pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 2307938Notes

Reaction equation

HRID 2307938 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=O.[NH2:16][C:17]1[NH:21][N:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=1>C(O)(=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]1[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[N:21]2[N:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=[C:17]2[N:16]=1

Participants

4

Reactant 2

HCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dioneHCID 178418848HCID 178418848, compound

Product 1

HCID 121332235-Pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4,4,4-Trifluoro-1-pyridin-2-yl-butane-1,3-dione (3.00 g, 13.8 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (1.76 g, 13.8 mmol) in acetic acid (100 ml) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 5-pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (3.04 g, 71%).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8013380646a348f7ad48684c4f074557
Source dataset
uspto-grants-2004_12
Patent number
US06833371B2

Reaction notes

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