Reaktion #65373

Reaktionsgleichung

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

PCl5

→

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

Ausbeute 63.8%

Lösungsmittel

POCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThereafter, the POCl3 was distilled off
2. 2
   Sonstigethe residue was partitioned between ethyl acetate and aqueous 1N NaOH
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 and chloroform
7. 7
   Sonstigerecrystallized from dichloromethane-ethanol

Vorschrift

4.57 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]benzenesulphonamide in 50 ml of POCl3 were stirred with 2.03 g of PCl5 at 20° C. for 2 hours. Thereafter, the POCl3 was distilled off and the residue was partitioned between ethyl acetate and aqueous 1N NaOH. The organic phase was washed with water, dried and the solvent was evaporated. The residue was chromatographed over silica gel with dichloromethane and chloroform, thereafter recrystallized from dichloromethane-ethanol. There were obtained 3.01 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p. 170° C., MS: M=581.

Quelle