Sodium Carbonate → 2-Chloro-5-(pyridin-2-yl)pyrimidine

HRID 988322Notes

Reaction equation

HRID 988322 reaction equation
C[N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[N:4][C:3]1=O.P(Cl)(Cl)(Cl)(Cl)[Cl:16].P(Cl)(Cl)(Cl)=O.C([O-])([O-])=O.[Na+].[Na+]>CO.O>[Cl:16][C:3]1[N:4]=[CH:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:7][N:2]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 22640307HCID 22640307, compound

Product 1

HCID 167263772-Chloro-5-(pyridin-2-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-methyl-5-(2-pyridinyl)-2(1H)pyrimidone (8.994 g, 0.048 mole), phosphorus pentachloride (2.156 g, 0.0104 mole), and phosphorus oxychloride (24 mL) was refluxed at 120° C. for 8 h. POCl3 was distilled out under reduced pressure. The residue was cooled to room temperature and ice-water was added. The mixture was extracted with EtOAc, the organic layer was washed with 15% NaCl solution, brine and dried over MgSO4. Solvent was distilled out under reduced pressure to yield a solid. The water layer was adjusted to pH 6-7 by using saturated Na2CO3, then extracted with EtOAc. The organic layer was washed with 15% NaCl, brine, dried over MgSO4. Solvent was distilled out under reduced pressure to give a solid. After trituration with MeOH, additional product was obtained.

Workup

  1. distillationPOCl3 was distilled out under reduced pressure
  2. temperatureThe residue was cooled to room temperature
  3. additionice-water was added
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organic layer was washed with 15% NaCl solution, brine
  6. dry with materialdried over MgSO4
  7. distillationSolvent was distilled out under reduced pressure
  8. customto yield a solid
  9. extractionextracted with EtOAc
  10. washThe organic layer was washed with 15% NaCl, brine
  11. dry with materialdried over MgSO4
  12. distillationSolvent was distilled out under reduced pressure
  13. customto give a solid

Sources & evidence

ORD record
ord-2f48b5d6b1b845929cd6bef1ae66d1f6
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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