Hydrogen Bromide → HCID 86268029, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-(4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-yl)-N,N-dimethylpyrrolidin-3-amine (0.10 g, 0.21 mmol) was dissolved in AcOH (3 mL) and then 48% hydrobromic acid (0.1 mL) was added. The mixture was heated at 90° C. for 3.5 hours. The mixture was concentrated and the residue was treated with NaHCO3 solution. The solution was extracted with EtOAc (3×) and the organic was washed with NaHCO3, dried over Na2SO4, filtered and concentrated to obtain the crude. The crude was treated with hot MeCN and kept at RT. The solid was filtered, washed with MeCN, and dried under vacuum to obtain (S)-2-(3-(dimethylamino)pyrrolidin-1-yl)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (62 mg, 62.8% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.29 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.53 (d, J=8.6 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.62 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 3.74 (m, 2H), 3.44 (m, 1H), 3.31 (s, 3H), 3.22 (m, 1H), 2.75 (m, 1H), 2.35 (s, 3H), 2.18 (s, 6H), 2.11 (m, 1H), 1.77 (m, 1H) one proton is missing; MS (ESI) m/z: 473.3 (M+H+).

Provenance & Evidence