Dimethylformamide → HCID 64178467, compound

HRID 537489Notes

Reaction equation

HRID 537489 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[F:9][C:10]([F:17])([F:16])[C:11]1[CH:12]=[N:13][NH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:13]2[CH:12]=[C:11]([C:10]([F:17])([F:16])[F:9])[CH:15]=[N:14]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 127777954-(Trifluoromethyl)-1H-pyrazole

Product 1

HCID 64178467HCID 64178467, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-bromo-2-chloropyrimidine (4.32 g, 21.5 mmol), 4-(trifluoromethyl)-1H-pyrazole (2.92 g, 21.5 mmol), and dried potassium carbonate (8.90 g, 64.4 mmol) was added anhydrous dimethylformamide (31.5 mL). The resulting suspension was heated at 85° C. for 4 h. The reaction was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give 12.4 g of crude yellow solid. The crude material was put through a plug of silica eluting with 15% ethyl acetate in heptanes to give 5-bromo-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (6.2 g, 99%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.83 (s, 2H), 8.02 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give 12.4 g of crude yellow solid

Sources & evidence

ORD record
ord-fa32804a291f4700a8ed2c8eda8bfeac
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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