2-(Dimethylamino)ethanol → N,N-Dimethyl-6-(tributylstannyl)pyridin-2-amine

Temperature

2.5 °C

To a solution of 2-dimethylaminoethanol (0.65 mL, 9.60 mmol) in hexane (10.0 mL, HPLC grade) cooled at −5° C. was added drop wise n-BuLi (1.60 M, 11.38 mL, 18.20 mmol) under nitrogen atmosphere. After 30 min at 0° C., dimethyl-pyridin-2-yl-amine (0.40 g, 3.20 mmol) in hexane (5.0 mL) was added drop wise. After stirring the reaction mixture for 1 h at 0-5° C., the reaction medium was cooled to −78° C. followed by drop wise addition of tributyl tin chloride (1.55 mL, 8.0 mmol). The resulting reaction mixture was stirred at −78° C. for 30 min and then allowed to stir at 0-5° C. for 1 h. The reaction mixture was then allowed to stir at room temperature for 16 h. After the completion of reaction (TLC monitoring), the reaction mass was cooled to 0° C. and water was added slowly. The aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness. The crude residue was carried foreard to the next step without further purification. MS: 413.22.

1. temperaturethe reaction medium was cooled to −78° C.
2. customThe resulting reaction mixture
3. stirringwas stirred at −78° C. for 30 min
4. stirringto stir at 0-5° C. for 1 h
5. stirringto stir at room temperature for 16 h
6. customAfter the completion of reaction (TLC monitoring)
7. temperaturethe reaction mass was cooled to 0° C.
8. extractionThe aqueous phase was extracted with diethyl ether (3×20 mL)
9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
10. customevaporated to dryness
11. customThe crude residue was carried foreard to the next step without further purification

ORD record

ord-0e74c2421c7548d4b84c1334816a3615

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977340B2