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 11879Notes

Reaction equation

HRID 11879 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 (3.00g, 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-28a5b5cc6d534df2ab307d50f454482a
Source dataset
uspto-grants-2006_08
Patent number
US07098335B2

Reaction notes

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