Reaktion #309248

Reaktionsgleichung

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

tert-butoxybis(dimethylamino) methane

→

desired product

Ausbeute 92.0%

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

Ausbeute 92.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDMF was partially removed
2. 2
   WaschenThe residue was washed with water
3. 3
   Extraktionextracted with ethyl acetate (×3)
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated to dryness

Vorschrift

To a homogenous mixture of 4-(4-(4-bromo-2,6-dimethylphenoxy)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile (22.71 g, 50 mmol) in DMF (300 ml) was added tert-butoxybis(dimethylamino) methane (12.39 ml, 60 mmol) over 15 minutes. The mixture was stirred at room temperature overnight. DMF was partially removed. The residue was washed with water and extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried (MgSO4) and concentrated to dryness yielding to the desired product as a yellow solid (23.41 g, 46.0 mmol, 92%) which was used in next step without further purification. 1H NMR (CDCl3, 400 MHz) δ2.14 (s, 6H), 2.98 (bs, 3H), 3.13 (bs, 3H), 5.54 (d, J=12.4 Hz, 1H), 7.03 (s, 1H), 7.27 (d, J=8.6, 2H), 7.28 (s, 2H), 7.40 (d, J=8.6, 2H), 8.03 (d, J=12.2 Hz, 1H).

Quelle