Potassium Carbonate → 2-Chloro-4-phenylpyrimidine

HRID 1678084Notes

Reaction equation

HRID 1678084 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[N:13]=[C:12](Cl)[CH:11]=[CH:10][N:9]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.CO.O.C(OC)(C)(C)C>[Cl:7][C:8]1[N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 775312,4-Dichloropyrimidine

Product 1

HCID 6053562-Chloro-4-phenylpyrimidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 23212559water MeOtBuSolvent

Procedure

2.78 g (20.14 mmol) of K2CO3, 0.21 g (0.18 mmol) of tetrakis(triphenylphosphine)Pd(0) were added to 1.00 g (6.71 mmol) of 2,4-dichloropyrimidine and 0.82 g (6.71 mmol) of benzeneboronic acid in 29 ml of toluene and 7 ml of methanol, and the reaction mixture was stirred at room temperature for 3 hours. The residue after concentration of the reaction mixture was taken up in water/methyl tert-butyl ether. The aqueous phase was then extracted twice with methyl tert-butyl ether. Thereafter the combined organic phase was washed with water and with a saturated aqueous NaCl solution, and the organic phase was dried, filtered to remove the desiccant and concentrated. The solid brown residue was purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane: 10:90); yield: 0.90 g.

Workup

  1. extractionThe aqueous phase was then extracted twice with methyl tert-butyl ether
  2. washThereafter the combined organic phase was washed with water and with a saturated aqueous NaCl solution
  3. customthe organic phase was dried
  4. filtrationfiltered
  5. customto remove the desiccant and
  6. concentrationconcentrated
  7. customThe solid brown residue was purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane: 10:90)

Sources & evidence

ORD record
ord-f731ac02822744189f3fb53536b43a1b
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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