Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile
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]=1Participants
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) w ith stirring. Th e hot hexane so lution 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-methylsulfanyl-pyrimidine.
Workup
- temperaturewas heated
- temperatureat reflux for 3 hours
- filtrationfiltered
- concentrationthe filtrate was concentrated to dryness under vacuum
- customThe residue was partitioned between methylene chloride and ice water
- customThe organic layer was separated
- washwashed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- temperatureThe residue was heated
- temperatureto reflux in hexane (750 mL)
- customTh e hot hexane so lution was decanted from the insoluble material
- temperatureto cool to room temperature
Sources & evidence
- ORD record
- ord-8ab8e4c5e12544e2968da84e6878580d
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05945422
Reaction notes
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