Potassium Carbonate → HCID 22340993, compound

HRID 1166043Notes

Reaction equation

HRID 1166043 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([C:16]2[C:20]([Cl:21])=[C:19]([S:22][CH:23]([F:25])[F:24])[N:18]([CH3:26])[N:17]=2)=[CH:11][C:10]=1[OH:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(C(C)=O)C>[Cl:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([C:16]2[C:20]([Cl:21])=[C:19]([S:22][CH:23]([F:25])[F:24])[N:18]([CH3:26])[N:17]=2)=[CH:11][C:10]=1[O:27][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 22341003HCID 22341003, compound

Product 1

HCID 22340993HCID 22340993, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-chloropyrimidine (150 mg), 2-chloro-5-[4-chloro-5-[(difluoromethyl)-thio]-1-methyl-1H-pyrazol-3-yl]-4-fluorophenol (0.3 g) and potassium carbonate (0.18 g) in N,N-dimethylformamide and methyl ethyl ketone (1:4, 20 ml) was heated at reflux overnight. The resulting mixture was allowed to cool to room temperature and partitioned between ethyl acetate and brine. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The organic solution was concentrated in vacuo and the residue purified by column chromatography on silica gel (eluent, ethyl acetate:hexane, 2:3) to give 2-[2-chloro-5-[4-chloro-5-[(difluoromethyl)thio]-1-methyl-1H-pyrazol-3-yl]-4-fluorophenoxy]pyrimidine, (0.29 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. custompartitioned between ethyl acetate and brine
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic solution was concentrated in vacuo
  7. customthe residue purified by column chromatography on silica gel (eluent, ethyl acetate:hexane, 2:3)

Sources & evidence

ORD record
ord-9dd712f06425445fa608b0079092defb
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

Loading…