Reaktion #1928625

Reaktionsgleichung

potassium carbonate

5-ethylamino-3-methylsulfanyl-1,2,4-triazine-6-carbaldehyde

3,5-dimethoxyphenylacetonitrile

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title compound

Ausbeute 60.0%

7-(3,5-Dimethoxy-phenyl)-5-ethyl-3-methylsulfanyl-5H-pyrido[2,3-e]-1,2,4-triazin-6-ylideneamine

Ausbeute 60.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under vacuum
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Waschenwashed three times with a saturated solution of sodium bicarbonate
4. 4
   TrocknenThe organic phase was dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Filtrationfiltered through celite
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give a dark orange oil
9. 9
   SonstigeThe crude oil was chromatographed through silica
10. 10
    Wascheneluted with 2:2:6 to 2:3:5 dichloromethane/ethyl acetate/hexane

Vorschrift

To a solution of 5.0 g (25.2 mmol) of 5-ethylamino-3-methylsulfanyl-1,2,4-triazine-6-carbaldehyde in 125 mL of THF was added 6.7 g (37.8 mmol) of 3,5-dimethoxyphenylacetonitrile followed by 17.4 g (126.1 mmol) of potassium carbonate. The reaction mixture was warmed at 65° C. for 2 days, concentrated under vacuum, diluted with ethyl acetate, and washed three times with a saturated solution of sodium bicarbonate, once with water and brine. The organic phase was dried over magnesium sulfate, filtered, decolorized with charcoal, filtered through celite, and concentrated to give a dark orange oil. The crude oil was chromatographed through silica eluted with 2:2:6 to 2:3:5 dichloromethane/ethyl acetate/hexane to give 5.4 g (59%) of the title compound as a yellow amorphous solid. MS (APCI) (m+1)/z 358.1.

Quelle