반응 #3267

반응 방정식

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

수율 40.0%

용매

methylene chloride

—

Petroleum ether

반응 조건

후처리

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

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