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Potassium Carbonate → [5-Methyl-2-[3-(trifluoromethyl)-1h-pyrazol-1-yl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanone

HRID 1060527
Notes
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Reaction equation

HRID 1060527 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:9])[C:5]([CH3:20])=[CH:4][N:3]=1.[F:21][C:22]([F:29])([F:28])[C:23]1[CH:27]=[CH:26][NH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][C:5]1[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:9])=[N:7][C:2]([N:25]2[CH:26]=[CH:27][C:23]([C:22]([F:29])([F:28])[F:21])=[N:24]2)=[N:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 18628524(2-Chloro-5-methyl-4-pyrimidinyl)[3-(trifluoromethyl)phenyl]methanone

Product 1

HCID 18628526[5-Methyl-2-[3-(trifluoromethyl)-1h-pyrazol-1-yl]-4-pyrimidinyl][3-(trifluoromethyl)phenyl]methanoneYield 16.3%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

The title compound of Step A (0.6 g, 2 mmol), 3-trifluoromethylpyrazole (0.25 g), and potassium carbonate (0.8 g, 6 mmol) were suspended in acetonitrile (15 mL) and heated at reflux for 3 h. The cooled reaction mixture was filtered and the cake washed with acetonitrile. After evaporation of the solvent under reduced pressure, the residue was subjected to silica gel chromatography using hexanes/ethyl acetate (85:15) to give 0.12 g of the title compound of Step B, a compound of the invention, as a white solid. 1H NMR (CDCl3/200 MHz) 2.45 (s, 3H), 6.75 (d, 1H), 7.67 (d, 1H), 7.92 (d, 1H), 8.10 (s, 1H), 8.27 (s, 1H), 8.54 (d, 1H), 8.9 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe cake washed with acetonitrile
  6. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0937343c6c8b4ab09c59e494c9bdf640
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06525001B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes