Potassium Carbonate → HCID 21267743, compound

HRID 565188Notes

Reaction equation

HRID 565188 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([F:17])([F:16])[C:11]1[CH:15]=[CH:14][NH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:13]2[CH:14]=[CH:15][C:11]([C:10]([F:17])([F:16])[F:9])=[N:12]2)[N:7]=1.[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]([N:13]2[CH:14]=[CH:15][C:11]([C:10]([F:17])([F:16])[F:9])=[N:12]2)[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 18070343-(Trifluoromethyl)pyrazole

Product 2

HCID 21267743HCID 21267743, compoundHCID 21267748HCID 21267748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dichloropyrimidine (3.0.g, 20 mmol), 3-(trifluoromethyl)-1H-pyrazole (2.5 g, 18 mmol) and potassium carbonate (5.0 g, 36 mmol) was stirred in 25 mL of N,N-dimethylformamide at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was washed twice with brine, dried over magnesium sulfate, and evaporated under reduced pressure to a crude solid. Flash chromatography on silica gel (50:1 to 25:1 to 110:1 to 3:1 hexane/ethyl acetate) afforded 0.5 g of the title compound of Step A as a solid melting at 123-125° C. and 2.3 g of the isomer 2-chloro-6-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidine as a solid melting at 111-112° C. 1H NMR (CDCl3): δ 6.77 (d, 1H), 7.35 (d, 1H), 8.65 (d, 1H), 8.70 (d, 1H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed twice with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure to a crude solid

Sources & evidence

ORD record
ord-17984e4114294db78f88f1ed4abe1a93
Source dataset
uspto-grants-2001_01
Patent number
US06172005B2

Reaction notes

Loading…