Potassium Carbonate → HCID 21267750, compound

HRID 565189Notes

Reaction equation

HRID 565189 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.[F:11][C:12]([F:19])([F:18])[C:13]1[CH:17]=[CH:16][NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC>[CH3:10][C:5]1[C:6]([S:8][CH3:9])=[N:7][C:2]([N:15]2[CH:16]=[CH:17][C:13]([C:12]([F:19])([F:18])[F:11])=[N:14]2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 21267740HCID 21267740, compound

Product 1

HCID 21267750HCID 21267750, compoundYield 350%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-5-methyl-4-methylthiopyrimidine (2.5 g, 14 mmol), 3-(trifluoromethyl)-1H-pyrazole (2.3 g, 2.5 mmol) and potassium carbonate (4.8 g, 35 mmol) in 25 mL of N,N-dimethylformamide was heated at 70° C. with stirring for 5 hours. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was separated, washed twice with water and brine and dried over magnesium sulfate. The solvent was removed under reduced pressure to provide a white solid which was suspended in hexane and filtered to provide 2.4 g of the title compound of Step B as a solid melting at 126-127° C. 1H NMR (CDCl3): δ 8.63 (d, 1H), 8.24 (s, 1H), 6.73 (d, 1H), 2.68 (s, 3H) 2.25 (s, 3H).

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed twice with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customto provide a white solid which
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6b0606f9acb04a0b8cd90f770b569a6c
Source dataset
uspto-grants-2001_01
Patent number
US06172005B2

Reaction notes

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