Реакция #3256

Уравнение реакции

5-cyano-4-hydroxy-2-methylsulfanylpyrimidine

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

phosphorus oxychloride

→

title compound

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

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 3 hours
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеthe filtrate was concentrated to dryness under vacuum
5. 5
   ДругоеThe residue was partitioned between methylene chloride and ice water
6. 6
   ДругоеThe organic layer was separated
7. 7
   Промывкаwashed with water
8. 8
   Сушкаdried over magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated under reduced pressure
11. 11
    ТемператураThe residue was heated
12. 12
    Температураto reflux in hexane (750 mL)
13. 13
    ДругоеThe hot hexane solution was decanted from the insoluble material
14. 14
    Температураto cool to room temperature

Методика

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.

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