4-Aminopyridine → HCID 69746753, compound

To a solution of t-butyldicarbonate (9.59 g) in THF (40 ml), 4-aminopyridine (3.76 g) was added. The mixture was stirred for 1 hour at room temperature. The solvent was distilled off from the reaction mixture. The obtained solid was washed with hexane/ethyl acetate (1:2), and the solid was obtained by filtration. To a solution of the obtained solid in THF (35 ml), 1.6M n-butyl lithium (9.6 ml) was added at −78° C., and then the mixture was stirred for 2 hours at 0° C. The mixture was cooled −78° C., and a solution of 4-bromo-1-methoxymethoxy-2-butene (1.5 g) in THF (4.0 ml) was dropped into the mixture slowly. The mixture was warmed until 10° C. under stirring for 2 hours. A saturated aqueous solution of ammonium chloride was added to the mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (394 mg) having the following physical data and 4-t-butoxycarbonylaminopyridine.

1. distillationThe solvent was distilled off from the reaction mixture
2. washThe obtained solid was washed with hexane/ethyl acetate (1:2)
3. customthe solid was obtained by filtration
4. stirringthe mixture was stirred for 2 hours at 0° C
5. temperatureThe mixture was cooled −78° C.
6. temperatureThe mixture was warmed until 10° C.
7. stirringunder stirring for 2 hours
8. extractionthe mixture was extracted with ethyl acetate
9. washThe organic layer was washed with water
10. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
11. concentrationconcentrated
12. customThe residue was purified by column chromatography on silica gel

ORD record

ord-bd13a65b65764b738c8494cfa654af48

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835752B2