Реакция #3267

Уравнение реакции

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

Выход 40.0%

Растворители

methylene chloride

—

Petroleum ether

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Фильтрацияthe solids were filtered
3. 3
   Промывкаwashed with ethyl acetate
4. 4
   КонцентрированиеThe filtrate was concentrated under reduced pressure
5. 5
   ДругоеThe residual gum was triturated with 10 mL of water
6. 6
   Фильтрацияthe resulting solid was filtered
7. 7
   Промывкаwashed well with water
8. 8
   Другоеdried
9. 9
   ДругоеThis crude material was chromatographed
10. 10
    ПромывкаThe column was eluted with 1:1 (v/v) hexane
11. 11
    Другоеethyl acetate, collecting the fractions that
12. 12
    ДругоеEvaporation of the solvents
13. 13
    Другоеgave a solid
14. 14
    Фильтрацияthe crystals were filtered

Методика

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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