Reaktion #323704

Reaktionsgleichung

2-amino-4,6-dichloropyrimidine

NaOCH3

→

product

Ausbeute 58.9%

2-Amino-4-chloro-6-methoxypyrimidine

Ausbeute 58.9%

Lösungsmittel

CH3OH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 10° with an ice bath
2. 2
   Temperaturwhile maintaining the temperature
3. 3
   Temperaturheated
4. 4
   Temperaturto reflux for two hours
5. 5
   Temperaturto cool to ambient temperature
6. 6
   FiltrationA yellow solid was filtered
7. 7
   Sonstigerecrystallized from butyl chloride
8. 8
   SonstigeThe resulting solid was chromatographed on a dry column of silica
9. 9
   Wascheneluted with 40% EtOAc-hexane
10. 10
    SonstigeThe resulting yellow solid was further purified by recrystallization from butyl chloride

Vorschrift

16.4 g 2-amino-4,6-dichloropyrimidine (purchased from Aldrich Chemical Co., Milwaukee, WI 53201) was added to 200 ml of CH3OH. The mixture was cooled to 10° with an ice bath and 5.4 g of NaOCH3 was added in portions while maintaining the temperature. The reaction mixture was allowed to warm to ambient temperature and then heated to reflux for two hours. The reaction mixture was then allowed to cool to ambient temperature and it was stirred overnight. A yellow solid was filtered and recrystallized from butyl chloride. The resulting solid was chromatographed on a dry column of silica, and eluted with 40% EtOAc-hexane. The resulting yellow solid was further purified by recrystallization from butyl chloride. 9.4 g of product with m.p. 163°-166° was obtained.

Quelle