Reacción #3256

Ecuación de reacción

5-cyano-4-hydroxy-2-methylsulfanylpyrimidine

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

phosphorus oxychloride

→

title compound

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 3 hours
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónthe filtrate was concentrated to dryness under vacuum
5. 5
   OtroThe residue was partitioned between methylene chloride and ice water
6. 6
   OtroThe organic layer was separated
7. 7
   Lavadowashed with water
8. 8
   Secadodried over magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated under reduced pressure
11. 11
    TemperaturaThe residue was heated
12. 12
    Temperaturato reflux in hexane (750 mL)
13. 13
    OtroThe hot hexane solution was decanted from the insoluble material
14. 14
    Temperaturato cool to room temperature

Procedimiento

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.

Fuente