Reaktion #81907

Reaktionsgleichung

Ethyl acetate

potassium carbonate

aldehyde

4-Methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde

2,6-dichlorophenylacetonitrile

dimethylformamide

→

6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine

Ausbeute 40.0%

Lösungsmittel

methylene chloride

—

Petroleum ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Filtrationthe solids were filtered
3. 3
   Waschenwashed with ethyl acetate
4. 4
   EinengenThe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe residual gum was triturated with 10 mL of water
6. 6
   Filtrationthe resulting solid was filtered
7. 7
   Waschenwashed well with water
8. 8
   Sonstigedried
9. 9
   SonstigeThis crude material was chromatographed
10. 10
    WaschenThe column was eluted with 1:1 (v/v) hexane
11. 11
    Sonstigeethyl acetate, collecting the fractions that
12. 12
    SonstigeEvaporation of the solvents
13. 13
    Sonstigegave a solid
14. 14
    Filtrationthe crystals were filtered

Vorschrift

Powdered potassium carbonate (0.8 g; 5.8 mmol) was added to a solution of 0.220 g (1.2 mmol) of the aldehyde from Example 18 and 0.235 g (1.26 mmol) (ca. 5% excess) of 2,6-dichlorophenylacetonitrile in 2.0 mL of dimethylformamide. The mixture was heated with stirring at 125° C. for 6 hours. Ethyl acetate (5 mL) was added to the cooled mixture, and the solids were filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residual gum was triturated with 10 mL of water, and the resulting solid was filtered, washed well with water, and dried. This crude material was chromatographed by placing a chloroform solution on a silica gel column wet with chloroform. The column was eluted with 1:1 (v/v) hexane:ethyl acetate, collecting the fractions that contain the Rf 0.25 spot on tlc (1:1 hexane:ethyl acetate). Evaporation of the solvents gave a solid. The solid product was dissolved in about 0.5 mL of methylene chloride. Crystals develop. Petroleum ether (ca. 2 mL) was added, and the crystals were filtered to provide 0.168 g (40%) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine, mp 198°-200° C.;

Quelle