2-(Dimethylamino)ethanol → 2-[(5-Bromo-2-pyridinyl)oxy]-N,N-dimethylethanamine

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 produt 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.

1. temperaturethe mixture heated
2. temperatureat reflux for 16 h
3. temperatureAfter cooling to room temperature
4. extractionthe mixture was extracted into 2 M aqueous HCl solution (30 mL)
5. washwashed with ethyl acetate (30 mL)
6. extractionthe produt extracted into ethylacetate (3×30 mL)
7. dry with materialThe organic layers were dried (MgSO4)

ORD record

ord-69afa63d98a84211b896346d7f76b8ed

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383620B2