Reaktion #58099

Reaktionsgleichung

2-chloro-4-(methylamino)-5-nitropyrimidine

tin(II) chloride dihydrate

→

title compound

Ausbeute 54.0%

5-amino-2-chloro-4-(methylamino)-pyrimidine

Ausbeute 54.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating for 2 hours
2. 2
   Temperaturthe reaction mixture is cooled to room temperature
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONEthyl acetate and celite is added to the residue
5. 5
   FiltrationThe mixture is filtered through a pad of celite
6. 6
   Waschenwashed with ethyl acetate
7. 7
   WaschenThe combined organic extracts are washed with brine
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigeFurther purification
12. 12
    Waschenby column chromatography (silica gel, eluting with ethyl acetate)

Vorschrift

A mixture of 2-chloro-4-(methylamino)-5-nitropyrimidine (3.76 g, 20 mmol, synthesized from the above procedure), tin(II) chloride dihydrate (18.0 g, 80 mmol) in ethanol (200 mL) is heated at 80° C. After heating for 2 hours, the reaction mixture is cooled to room temperature and concentrated. Ethyl acetate and celite is added to the residue and the mixture is basified with saturated sodium carbonate solution to a pH of 9-10. The mixture is filtered through a pad of celite and washed with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. Further purification by column chromatography (silica gel, eluting with ethyl acetate) affords the title compound (1.72 g, 54%).

Quelle