2-(Dimethylamino)ethanol → 6-[2-(Dimethylamino)ethoxy]pyridin-3-amine

To a solution of 2-chloro-5-nitropyridine (500 mg, 3.1 mmol) in dioxane (30 mL) at room temperature was added 2-(dimethylamino)ethanol (309 mg, 3.5 mmol) and 60 wt. % NaH (0.15 g, 3.7 mmol) and the reaction mixture was stirred at room temperature until the reaction was complete by LCMS analysis. The reaction mixture was poured onto ice-cold water and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated. The residue was dissolved in tetrahydrofuran (30 mL), degassed with nitrogen, charged with catalytic 10 wt. % Pd/C (0.3 g) and the reaction mixture was placed under an atmosphere of hydrogen (40 Psi) until the reduction was complete by LCMS analysis. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated to provide the desired product (340 mg, 61%) as a purple solid: ESI MS m/z 182 [C9H15N3O+H]+.

1. additionThe reaction mixture was poured onto ice-cold water
2. extractionthe product was extracted with dichloromethane
3. dry with materialThe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. dissolutionThe residue was dissolved in tetrahydrofuran (30 mL)
7. customdegassed with nitrogen
8. additioncharged with catalytic 10 wt. % Pd/C (0.3 g)
9. filtrationThe reaction mixture was filtered over diatomaceous earth
10. concentrationthe filtrate was concentrated

ORD record

ord-36b05c3902c144b8ad897d5d2fe03d78

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067937B2