反応 #3267

反応方程式

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

収率 40.0%

溶媒

methylene chloride

—

Petroleum ether

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   ろ過the solids were filtered
3. 3
   洗浄washed with ethyl acetate
4. 4
   濃縮The filtrate was concentrated under reduced pressure
5. 5
   その他The residual gum was triturated with 10 mL of water
6. 6
   ろ過the resulting solid was filtered
7. 7
   洗浄washed well with water
8. 8
   その他dried
9. 9
   その他This crude material was chromatographed
10. 10
    洗浄The column was eluted with 1:1 (v/v) hexane
11. 11
    その他ethyl acetate, collecting the fractions that
12. 12
    その他Evaporation of the solvents
13. 13
    その他gave a solid
14. 14
    ろ過the crystals were filtered

実験手順

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.

出典