Diisopropyl Ether → 4-Benzyl-2-methoxypyridin-3-amine

To a solution of tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate (25.4 g) in ethyl acetate (202 mL) was added 4N hydrogen chloride/ethyl acetate solution (202 mL) at room temperature, and the mixture was stirred overnight at room temperature, and then at 50° C. for 1 hr. To the reaction mixture was added diisopropyl ether at room temperature, and the obtained precipitate was collected by filtration, and washed with diisopropyl ether. Saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane) to give the title compound (8.8 g).

1. waitat 50° C. for 1 hr
2. filtrationthe obtained precipitate was collected by filtration
3. washwashed with diisopropyl ether
4. additionSaturated aqueous sodium hydrogencarbonate solution was added
5. extractionthe mixture was extracted with ethyl acetate
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)

ORD record

ord-4e05ceae2f584ab799142f2ef9fe2878

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371320B2