Reaktion #2025720

Reaktionsgleichung

2,6-dichloro-4-(3,4-methylenedioxybenzyl)aminoquinazoline

sodium hydride

5-hydroxy-2-phenyl-1,3-dioxane

dimethylformamide

→

2-(2-phenyl-1,3-dioxan-5-yl)oxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

Ausbeute 27.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe obtained mixture was heated at 140° C. for 2 hours
2. 2
   Temperaturcooled
3. 3
   ExtraktionThe obtained mixture was extracted with ethyl acetate
4. 4
   SonstigeThe extract was purified by silica gel column chromatography

Vorschrift

100 mg of sodium hydride was added to a mixture comprising 300 mg of 5-hydroxy-2-phenyl-1,3-dioxane and 5 ml of dimethylformamide. The obtained mixture was heated to 80° C. After the bubbling had been discontinued, 300 mg of 2,6-dichloro-4-(3,4-methylenedioxybenzyl)aminoquinazoline was added in a crystalline state. The obtained mixture was heated at 140° C. for 2 hours and cooled, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography using an ethyl acetate/benzene mixture to give 118 mg of 2-(2-phenyl-1,3-dioxan-5-yl)oxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. 100 mg of this compound was hydrolyzed with concentrated hydrochloric acid/ethanol by a conventional process to give 60 mg of the title compound through rearrangement.

Quelle