Potassium Carbonate → 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine

HRID 537458Notes

Reaction equation

HRID 537458 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:19])([F:18])[C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([N:15]2[CH:14]=[C:13]([C:12]([F:19])([F:18])[F:11])[CH:17]=[N:16]2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 825442-Chloro-5-nitropyrimidineHCID 127777954-(Trifluoromethyl)-1H-pyrazole

Product 1

HCID 681573265-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidineYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-nitropyrimidine (1.5 g, 9.4 mmol) and 4-(trifluoromethyl)-1H-pyrazole (1.41 g, 10.3 mmol) in acetonitrile (40 mL) was added potassium carbonate (2.60 g, 18.8 mmol). The reaction was heated to 80° C. and stirred overnight. The reaction was concentrated and the residue was diluted with water and extracted with ethyl acetate (2×40 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.5 g, 62%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 9.48 (s, 2H), 8.92 (s, 1H), 8.05 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-55967013afae432fa9fd3a61c15fd60c
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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