Réaction #3256

Équation de réaction

5-cyano-4-hydroxy-2-methylsulfanylpyrimidine

5-cyano-4-hydroxy-2-methylsulfanyl-pyrimidine

phosphorus oxychloride

→

title compound

4-Chloro-5-cyano-2-methylsulfanyl-pyrimidine

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 3 hours
3. 3
   Filtrationfiltered
4. 4
   Concentrationthe filtrate was concentrated to dryness under vacuum
5. 5
   AutreThe residue was partitioned between methylene chloride and ice water
6. 6
   AutreThe organic layer was separated
7. 7
   Lavagewashed with water
8. 8
   Séchagedried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated under reduced pressure
11. 11
    TempératureThe residue was heated
12. 12
    Températureto reflux in hexane (750 mL)
13. 13
    AutreThe hot hexane solution was decanted from the insoluble material
14. 14
    Températureto cool to room temperature

Mode opératoire

A mixture of 5-cyano-4-hydroxy-2-methylsulfanylpyrimidine (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-methylsulfanyl-pyrimidine.

Source