Hydrogen Bromide → HCID 86268246, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(tert-butyl)-4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.069 g, 0.155 mmol) in acetic acid (1.5 mL) was treated with HBr (48% aq., 0.071 mL, 0.623 mmol) and heated at 90° C. for 4 h. The mixture was removed from heat, treated with ice and EtOAc, neutralized with satd. NaHCO3, extracted with 1:1 EtOAc/THF (3×) and the combined organics were washed with brine, dried over MgSO4 and concentrated to dryness. The resulting material was treated with MeCN, heated to near-reflux and allowed to stand at RT overnight. The solid was removed via filtration and the filtrate was concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM, then MeOH/EtOAc) to afford 2-(tert-butylamino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (11 mg, 15%). 1H NMR (400 MHz, DMSO-d6): δ 10.59 (s, 1H), 8.67 (s, 1H), 8.37 (d, J=5.6 Hz, 1H), 8.27-8.22 (m, 2H), 7.97 (s, 1H), 7.52 (d, J=8.9 Hz, 1H), 7.23 (d, J=2.6 Hz, 1H), 6.60 (dd, J=6.1, 2.6 Hz, 1H), 6.52 (s, 1H), 3.84 (s, 3H), 2.34 (s, 3H), 1.41 (s, 9H); MS (ESI) m/z: 432.2 (M+H+).

Provenance & Evidence