Ethyl Acetate → HCID 178448113, compound

Participants

Reaction Steps

Under a N2 atmosphere, 142 μl (1.02 mmol) of trimethylsilyl iodide are added to 400 mg (1.02 mmol) of trans 5-(4-isopropyl-cyclohexylamino)-8-[(6-methoxy-pyridin-3-yl)-methyl]-[1,6]naphthyridine in 7 ml of chloroform, and stirring is effected for 12 h at 70° C. The mixture is cooled, EtOAc and diluted NaHCO3 are added, stirring is effected until everything has dissolved, the organic phase is separated and washed with water and brine. The aqueous phases are extracted twice more with EtOAc. Drying (Na2SO4), concentrating by evaporation, column chromatography (SiO2, EtOAc/EtOH 5:1) and stirring with DIPE yield trans 5-(4-isopropyl-cyclohexylamino)-8-[(6-hydroxy-pyridin-3-yl)-methyl]-[1,6]naphthyridine; m.p. 232-235° C.; FAB-MS: (M+H)+=377.

Provenance & Evidence