Reaktion #162710

Reaktionsgleichung

4-{[(1S,2R)-2-aminocyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide

cyanogen bromide

Water

→

desired compound

Ausbeute 55.5%

4-{[(1S,2R)-2-(cyanoamino)cyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide

Ausbeute 55.5%

Lösungsmittel

tetrahydrofuran

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was subjected to an extraction with ethyl acetate
2. 2
   WaschenThe organic layer was washed with water and saturated brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Vorschrift

In an argon atmosphere, to a solution of 3.30 g of 4-{[(1S,2R)-2-aminocyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide in 80 ml of tetrahydrofuran, 1.54 ml of triethylamine and 978 mg of cyanogen bromide were sequentially added at −20° C., and the mixture was stirred at the same temperature for 0.5 hour. Water was added to the reaction solution, and the mixture was subjected to an extraction with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1), whereby 1.96 g of a desired compound was obtained as a pale yellow crystal.

Quelle