反应详情

温度

125 °C

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.;

1. temperatureThe mixture was heated
2. filtrationthe solids were filtered
3. washwashed with ethyl acetate
4. concentrationThe filtrate was concentrated under reduced pressure
5. customThe residual gum was triturated with 10 mL of water
6. filtrationthe resulting solid was filtered
7. washwashed well with water
8. customdried
9. customThis crude material was chromatographed
10. washThe column was eluted with 1:1 (v/v) hexane
11. customethyl acetate, collecting the fractions that
12. customEvaporation of the solvents
13. customgave a solid
14. filtrationthe crystals were filtered