Sodium Carbonate → 4-Chloro-6-(2-methoxyphenyl)pyrimidine

HRID 2063611Notes

Reaction equation

HRID 2063611 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 152068354-Chloro-6-(2-methoxyphenyl)pyrimidineYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4,6-dichloropyrimidine (2.0 g, 13 mmol), 2-methoxyphenylboronic acid (2.0 g, 13 mmol), and sodium carbonate (4.4 g, 42 mmol, dissolved in minimal amount of water) was degassed with argon. To the degassed solution Pd(Ph3)4 was added and the resultant reaction mixture was refluxed for 18 hours. The reaction mixture was cooled to room temperature and diluted with dichloromethane. The organics were washed with water and the aqueous layer was extracted with additional dichloromethane. The combined organics were washed with brine and dried over sodium sulfate. Following filtration, the organics were dried in vacuo and the residue was purified by Si gel chromatography (1:10 ethyl acetate:hexanes) to yield 2.4 g (80%) of the title compound.

Workup

  1. customthe resultant reaction mixture
  2. temperaturewas refluxed for 18 hours
  3. washThe organics were washed with water
  4. extractionthe aqueous layer was extracted with additional dichloromethane
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltration
  8. customthe organics were dried in vacuo
  9. customthe residue was purified by Si gel chromatography (1:10 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-c086f0a8bc984c35a8371389f1bf8556
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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