تفاعل #3267

معادلة التفاعل

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

المردود 40.0%

المذيبات

methylene chloride

—

Petroleum ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   ترشيحthe solids were filtered
3. 3
   غسيلwashed with ethyl acetate
4. 4
   تركيزThe filtrate was concentrated under reduced pressure
5. 5
   أخرىThe residual gum was triturated with 10 mL of water
6. 6
   ترشيحthe resulting solid was filtered
7. 7
   غسيلwashed well with water
8. 8
   أخرىdried
9. 9
   أخرىThis crude material was chromatographed
10. 10
    غسيلThe column was eluted with 1:1 (v/v) hexane
11. 11
    أخرىethyl acetate, collecting the fractions that
12. 12
    أخرىEvaporation of the solvents
13. 13
    أخرىgave a solid
14. 14
    ترشيحthe crystals were filtered

الإجراء التجريبي

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.

المصدر