Reaktion #309253

Reaktionsgleichung

methyl 4-(4-(4-bromo-2,6-dimethylphenylamino)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile

tert-butoxybis(dimethylamino)methane

→

(E)-4-(4-(4-bromo-2,6-dimethylphenylamino)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2-ylamino)benzonitrile

Ausbeute 67.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUpon completion the reaction was cooled to ambient temperature
2. 2
   Einengenconcentrated to half volume
3. 3
   Sonstigequenched with H2O (100 ml)
4. 4
   ExtraktionThe aqueous solution was extracted with ethyl acetate (3×70 ml)
5. 5
   Waschenthe collected organic fractions were washed with brine (100 ml)
6. 6
   Trocknendried with MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

A dried flask under argon was charged with methyl 4-(4-(4-bromo-2,6-dimethylphenylamino)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile (4.3 g, 9.5 mmol) dissolved in anhydrous DMF (95 ml) followed by tert-butoxybis(dimethylamino)methane (2.4 ml, 11.4 mmol). The reaction mixture was heated to 60° C. and stirred overnight under argon. Upon completion the reaction was cooled to ambient temperature, concentrated to half volume, and quenched with H2O (100 ml). The aqueous solution was extracted with ethyl acetate (3×70 ml) and the collected organic fractions were washed with brine (100 ml), dried with MgSO4, filtered and concentrated. Silica gel chromatography (ethyl acetate: Hexanes=50:50) yielded (E)-4-(4-(4-bromo-2,6-dimethylphenylamino)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2-ylamino)benzonitrile (3.21 g, 67%) as a brown solid. m/z=508 [M+1].

Quelle