Potassium Carbonate → 2-(2,6-Difluorophenyl)-5-(4'-trifluoromethoxybiphenyl-4-yl)-pyrimidine

HRID 2119786Notes

Reaction equation

HRID 2119786 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:36])([F:35])[O:24][C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.CC(O)=O.CC(O)=O.[Pd]>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:11]1[N:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]([F:22])([F:35])[F:36])=[CH:30][CH:29]=3)=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 227270174-Trifluoromethoxyphenylboric acidHCID 234433995-(4-Bromophenyl)-2-(2,6-difluorophenyl)-pyrimidine

Product 1

HCID 114077102-(2,6-Difluorophenyl)-5-(4'-trifluoromethoxybiphenyl-4-yl)-pyrimidine

Reagents, catalysts & solvents 3

HCID 4144353Palladium (II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.70 g of 5-(4-bromophenyl)-2-(2,6-difluorophenyl)-pyrimidine, 0.53 g of 4-trifluoromethoxyphenyl-boric acid and 0.07 g of palladium-II-acetate are heated under reflux for 1½ hours, under nitrogen, in a mixture of 20 ml of dimethoxyethane and 20 ml of saturated, aqueous potassium carbonate solution. The reaction mixture is then cooled, diluted with water and the crystalline precipitate filtered. After dissolving the precipitate in ethyl acetate, drying with magnesium sulfate, filtering and concentrating, the title compound is obtained in the form of light yellow crystals with a melting point of 215-216° C.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationthe crystalline precipitate filtered
  3. dissolutionAfter dissolving the precipitate in ethyl acetate
  4. dry with materialdrying with magnesium sulfate
  5. filtrationfiltering
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-7250a6f371b7471ab478931cd22d12ef
Source dataset
uspto-grants-2004_02
Patent number
US06686469B2

Reaction notes

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