반응 #81907
ord-3c1ba819d1914d3589c7b7c92e2c4cb5
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후처리
- 1온도The mixture was heated
- 2여과the solids were filtered
- 3세척washed with ethyl acetate
- 4농축The filtrate was concentrated under reduced pressure
- 5기타The residual gum was triturated with 10 mL of water
- 6여과the resulting solid was filtered
- 7세척washed well with water
- 8기타dried
- 9기타This crude material was chromatographed
- 10세척The column was eluted with 1:1 (v/v) hexane
- 11기타ethyl acetate, collecting the fractions that
- 12기타Evaporation of the solvents
- 13기타gave a solid
- 14여과the crystals were filtered
실험 절차
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.;