Triphenylphosphine → 4-Chloro-6-(3-chloro-4-trifluoromethyl-phenyl)pyrimidine

HRID 1908230Notes

Reaction equation

HRID 1908230 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=1[C:35]([F:38])([F:37])[F:36].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:8][C:6]1[CH:7]=[C:2]([C:31]2[CH:32]=[CH:33][C:34]([C:35]([F:37])([F:38])[F:36])=[C:29]([Cl:28])[CH:30]=2)[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 709434,6-DichloropyrimidineHCID 37729583-Chloro-4-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 249021774-Chloro-6-(3-chloro-4-trifluoromethyl-phenyl)pyrimidineYield 35.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of CH3CN and water (75:25 mL) that has been degassed by bubbling N2 into the solvent were added 4,6-dichloro-pyrimidine (3.63 g, 22.7 mmol) and Ph3P (840 mg, 2.2 mmol). De-gassing was continued for an additional 15 min before adding 3-chloro-4-trifluoromethylphenyl boronic acid (5 g, 22 mmol), Pd (OAc)2 (250 mg, 1.11 mmol) and K3PO4 (9.4 g, 44.3 mmol). The resulting mixture was stirred at rt for 2 h before diluting with water and extracting with EtOAc. The organic layer was dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (2.3 g, 35%).

Workup

  1. customTo a solution of CH3CN and water (75:25 mL) that has been degassed
  2. customby bubbling N2 into the solvent
  3. customDe-gassing
  4. extractionextracting with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-d2ac7a481fdb4e9791fe94590982c105
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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