Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

HRID 53617Notes

Reaction equation

HRID 53617 reaction equation
[C:1]([C:3]1[C:4](O)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#[N:2].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:4]1[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418413HCID 178418413, compound

Product 1

HCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Procedure

A mixture of 5-cyano-4-hydroxy-2-methylsulfanyl-pyrimidine (48.33 g) from Example 1 and phosphorus oxychloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated to dryness under vacuum. The residue was partitioned between methylene chloride and ice water. The organic layer was separated, washed with water, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was heated to reflux in hexane (750 mL) with stirring. The hot hexane solution was decanted from the insoluble material and allowed to cool to room temperature to afford 32 g of the title compound 4-chloro-5-cyano-2-methysulfanyl-pyrimidine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness under vacuum
  5. customThe residue was partitioned between methylene chloride and ice water
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. temperatureThe residue was heated
  12. temperatureto reflux in hexane (750 mL)
  13. customThe hot hexane solution was decanted from the insoluble material
  14. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-bab463ea2fb44a65a57199d30593a02d
Source dataset
uspto-grants-1997_04
Patent number
US05620981

Reaction notes

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