Reaktion #366681

Reaktionsgleichung

4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

potassium carbonate

4-(bromomethyl)pyridine hydrobromide

→

4-(3-acetoxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline

Ausbeute 22.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated
2. 2
   Sonstigethe residue was partitioned between ethyl acetate and water
3. 3
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column flash chromatography
7. 7
   Wascheneluting with methylene chloride/methanol (95/5)

Vorschrift

To a solution of 4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (375 mg, 1 mmol) in DMF (16 ml) were added at ambient temperature potassium carbonate (415 mg, 3 mmol) and 4-(bromomethyl)pyridine hydrobromide (J.Org.Chem. 1958, 23, 575, 278 mg, 1.1 mmol). The reaction mixture was heated at 60° C. for 2 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column flash chromatography, eluting with methylene chloride/methanol (95/5) to give 4-(3-acetoxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline (93 mg, 22%).

Quelle