2-(Dimethylamino)ethanol → 2-[(5-Bromo-2-pyridinyl)oxy]-N,N-dimethylethanamine
Reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[CH:11]=N[C:13](Cl)=[N:14][CH:15]=1.[CH2:17]1COCC1>>[Br:9][C:10]1[CH:11]=[CH:17][C:13]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:14][CH:15]=1Participants
5
Procedure
To a solution of N,N-dimethylethanolamine (0.36 mL) in THF (15 mL) was added sodium hydride (145 mg). After stirring at room temperature for 10 minutes, 5-bromo-2-chloropyrimidine (500 mg) was added and the mixture heated at reflux for 16 h. After cooling to room temperature, the mixture was extracted into 2 M aqueous HCl solution (30 mL) and washed with ethyl acetate (30 mL) The aqueous layer was made basic with sodium carbonate and the product extracted into ethylacetate (3×30 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give [2-(5-bromo-pyridin-2-yloxy)-ethyl]-dimethylamine as a white solid.