Hydrochloric Acid → 5-Bromo-3-[5-(1-ethylamino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

Participants

Reaction Steps

N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide (417 mg, 1.1 mmol) was dissolved in THF (40 ml). This solution was refluxed and 10 M borane dimethyl sulfide complex (165 μl, 1.65 mmol) was added slowly to the refluxing mixture. The reaction mixture was refluxed for 2.5 hr. Next, 0.5 ml 6 M hydrochloric acid solution was added and after stirring at reflux for 5 min it was cooled to room temperature. Next 3M sodium hydroxide solution was added, followed by water and the material was extracted with ethyl acetate. It was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by silica gel chromatography 0-10% MeOH in DCM to give 5-Bromo-3-[5-(1-ethylamino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one (73 mg, 18%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.14 (t, J=7.18 Hz, 3 H) 1.70 (s, 6 H) 2.67 (m, 2 H) 3.52 (s, 3 H) 7.44 (d, J=9.06 Hz, 1 H) 7.58 (d, J=2.27 Hz, 1 H) 7.86 (dd, J=8.69, 2.64 Hz, 1 H) 8.45 (d, J=2.64 Hz, 1 H) 8.73 (d, J=2.64 Hz, 1 H) 8.76-8.88 (m, 1 H) 8.99 (s, 1 H).

Provenance & Evidence