Reaktion #69967

Reaktionsgleichung

4-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid

2-(chloromethyl)pyrimidine

potassium carbonate

potassium carbonate

→

1-[4-(pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydro-quinoxaline

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheating
2. 2
   Temperaturis maintained for 1 h 30
3. 3
   SonstigeAfter hydrolysis
4. 4
   Extraktionthe reaction medium is extracted with ethyl acetate until the aqueous phase
5. 5
   Extraktionhas been completely extracted
6. 6
   Waschenwashed with a saturated aqueous sodium chloride solution
7. 7
   Trocknendried over magnesium sulphate
8. 8
   Einengenconcentrated to dryness
9. 9
   SonstigeThe crude product obtained
10. 10
    Sonstigeis chromatographed on silica gel, elution

Vorschrift

0.3 g of the tent-Butyl ester of 4-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid is placed in 4.6 ml of dimethylformamide under nitrogen. 0.167 g of 2-(chloromethyl)pyrimidine and 0.508 g of potassium carbonate are added. The reaction medium is heated at 100° C. for 4 h. 0.254 g of potassium carbonate is added and heating is maintained for 1 h 30. After hydrolysis, the reaction medium is extracted with ethyl acetate until the aqueous phase has been completely extracted. The organic phases are combined, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 9/1. 0.095 g of 1-[4-(pyrimidin-2-ylmethoxy)phenyl]-1,2,3,4-tetrahydro-quinoxaline is obtained.

Quelle