Reaktion #956182

Reaktionsgleichung

1,6-naphthyridin-5-amine

1,3-dichloropropan-2-one

→

2-(chloromethyl)imidazo[2,1-f][1,6]naphthyridine

Ausbeute 59.7%

Lösungsmittel

EtOH

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONThe solid dissolved immediately
2. 2
   Temperaturwas cooled to 0° C. for 20 min
3. 3
   FiltrationThe resulting mixture was filtered
4. 4
   Sonstigeto give a white solid
5. 5
   Temperaturheated
6. 6
   Temperaturat reflux
7. 7
   TemperaturAfter refluxing for 2 h
8. 8
   Einengenthe reaction mixture was concentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in water
10. 10
    workup.ADDITIONsaturated aqueous NaHCO3 solution was added
11. 11
    SonstigeA white suspension formed during the course of addition
12. 12
    workup.STIRRINGThe resulting mixture was stirred for 20 min
13. 13
    Filtrationfiltered

Vorschrift

To a solution of 1,6-naphthyridin-5-amine (145 mg, 1 mmol) in 1,2-dimethoxyethane (5 mL) was added 1,3-dichloropropan-2-one (140 mg, 1.1 mmol). The solid dissolved immediately and a white precipitate was observed. The mixture was stirred at room temperature for 1 h, and then was cooled to 0° C. for 20 min. The resulting mixture was filtered to give a white solid. The precipitate was suspended in EtOH (40 mL) and heated at reflux. After refluxing for 2 h, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and saturated aqueous NaHCO3 solution was added to adjust the pH value to 7. A white suspension formed during the course of addition. The resulting mixture was stirred for 20 min and then filtered to give 2-(chloromethyl)imidazo[2,1-f][1,6]naphthyridine as a white solid (130 mg). MS (ESI): m/z 218 [M+H]+.

Quelle