反应 #81907
ord-3c1ba819d1914d3589c7b7c92e2c4cb5
反应方程式
反应物
试剂
反应条件
后处理
- 1温度The mixture was heated
- 2过滤the solids were filtered
- 3洗涤washed with ethyl acetate
- 4浓缩The filtrate was concentrated under reduced pressure
- 5其他The residual gum was triturated with 10 mL of water
- 6过滤the resulting solid was filtered
- 7洗涤washed well with water
- 8其他dried
- 9其他This crude material was chromatographed
- 10洗涤The column was eluted with 1:1 (v/v) hexane
- 11其他ethyl acetate, collecting the fractions that
- 12其他Evaporation of the solvents
- 13其他gave a solid
- 14过滤the crystals were filtered
实验过程
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.;