Reaktion #61390

Reaktionsgleichung

benzamidine

Ethyl(ethoxymethylene)cyanoacetate

→

4-hydroxy-2-phenyl-pyrimidine-5-carbonitrile

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturincrease to 105° C. for 60 h
2. 2
   TemperaturThe reaction mixture was then cooled to ambient temperature
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate (2×100 mL )
4. 4
   WaschenThe combined organic extracts were washed with water (1×50 mL) and brine (1×50 mL)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo
8. 8
   WaschenThe residue was washed with water (1×60 mL), dichloromethane (1×60 mL)
9. 9
   Sonstigethen dried in the vacuum oven
10. 10
    Sonstigeto obtain the light yellow solid as product (0.77 g, 47%)

Vorschrift

To a stirred solution of benzamidine (1.0 g, 8.32 mmol) in anhydrous DMF (20 mL ) was added Ethyl(ethoxymethylene)cyanoacetate (11) (1.41 g, 8.32 mmol, 1.0 equiv ) under argon at 0° C. The mixture was stirred at 0° C. for 2 h and increase to 105° C. for 60 h. The reaction mixture was then cooled to ambient temperature. The mixture was extracted with ethyl acetate (2×100 mL ). The combined organic extracts were washed with water (1×50 mL) and brine (1×50 mL), dried (Na2SO4), filtered, and evaporated in vacuo. The residue was washed with water (1×60 mL), dichloromethane (1×60 mL) then dried in the vacuum oven to obtain the light yellow solid as product (0.77 g, 47%). 1H-NMR (CD3CN) δ8.25 (s, 1H ), 8.06 (d, 2H ), 7.70 (t, 1H ), 7.61 (t, 2H). MS LC-MS (MH+=198).

Quelle