Reaktion #65372

Reaktionsgleichung

4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

sodium borohydride

→

4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

Ausbeute 65.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThereafter, the ethanol was distilled off
2. 2
   Sonstigethe residue was partitioned between chloroform and 1N HCI
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Sonstigedried
5. 5
   Sonstigethe solvent was evaporated
6. 6
   Sonstigethe residue was chromatographed over silica gel with dichloromethane
7. 7
   SonstigeAfter recrystallization from dichloromethane-ethanol there

Vorschrift

7 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide in 300 mi of ethanol were treated with 0.9 g of sodium borohydride. The reaction mixture was stirred at 80° C. for 1 hour. Thereafter, the ethanol was distilled off and the residue was partitioned between chloroform and 1N HCI. The organic phase was washed with water and dried, the solvent was evaporated and the residue was chromatographed over silica gel with dichloromethane. After recrystallization from dichloromethane-ethanol there were obtained 4.6 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p. 103° C., MS: M=563.

Quelle