Hydrochloric Acid → HCID 86641279, compound

To a solution of ethyl 5-(tert-butoxycarbonylamino)-6-iodo-4-methylpyridine-2-carboxylate (1.94 g) in toluene (48 mL) was added diisobutylaluminium hydride (0.99 mol/L toluene solution, 25 mL) at −78° C., and the mixture was stirred under ice-cooling for 2 hours, and then stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=9/1−1/9) to give 3-(tert-butoxycarbonylamino)-6-hydroxymethyl-2-iodo-4-methylpyridine (1 g). This material was dissolved in N,N-dimethylformamide (5 mL). To the solution were added imidazole (0.24 g) and tert-butyldimethylchlorosilane (0.46 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=7/3) to give the title compound (1.3 g).

1. temperaturecooling for 2 hours
2. stirringstirred at room temperature overnight
3. extractionthe resulting mixture was extracted with ethyl acetate
4. washThe extract was washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed under reduced pressure
7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=9/1−1/9)

ORD record

ord-5c623b218cf54bd1937073b17e71db1b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217069B2