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

HRID 2420988Notes

Reaction equation

HRID 2420988 reaction equation
[C:1]([C:3]1[C:4](=O)[NH: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 27278634-hydroxy-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileYield 40%

Procedure

Phosphorus oxychloride (150 mL) was added to 5-cyano-3,4-dihydro-2-methylthiopyrimidin-4-one (30.0 g, 0.159 mmol) obtained in Step 1, and the mixture was heated under reflux for 7 hours. The reaction mixture was left to stand to cool, and then phosphorus oxychloride was evaporated under reduced pressure. The residue was poured into ice water (about 1,000 mL), and the precipitated light yellow solid was collected by filtration and washed with water. The resulting solid was dried under reduced pressure to give 4-chloro-5-cyano-2-methylthiopyrimidine (11.9 g, yield 40%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. customphosphorus oxychloride was evaporated under reduced pressure
  6. additionThe residue was poured into ice water (about 1,000 mL)
  7. filtrationthe precipitated light yellow solid was collected by filtration
  8. washwashed with water
  9. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-8a8260167ac0461a80c05333007b7e10
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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