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

HRID 1783505Notes

Reaction equation

HRID 1783505 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418413HCID 178418413, compound

Product 1

HCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileYield 60%

Procedure

A mixture of 48.3 g (289 mmol) of 4-hydroxy-2-(methylthio)-5-pyrimidinecarbonitrile and 150 mL of phosphorus oxychloride is heated at reflux for 3 hours. The reaction mixture is cooled to room temperature, filtered, and the filtrate is concentrated to dryness. The residue is partitioned between dichloromethane and ice water. The organic phase is washed with water, dried over magnesium sulfate, and concentrated to a residue that is diluted with 750 mL of hexane. The stirred mixture is heated to reflux and the hot hexane solution is decanted from the insoluble material. Upon cooling to room temperature, crystals form and are collected to afford 32 g (60%) of the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated to dryness
  5. customThe residue is partitioned between dichloromethane and ice water
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to a residue that
  9. additionis diluted with 750 mL of hexane
  10. temperatureThe stirred mixture is heated
  11. temperatureto reflux
  12. customthe hot hexane solution is decanted from the insoluble material
  13. temperatureUpon cooling to room temperature
  14. customcrystals form and are collected

Sources & evidence

ORD record
ord-085c9f84ee6d4625b6528446c447a9cb
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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