Hydrogen Bromide → HCID 86267408, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methoxy-N-(2-methoxyethyl)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.10 g, 0.22 mmol) in acetic acid (5 mL) was treated with HBr (0.10 mL, 0.90 mmol), heated at 90° C. for 4 h, cooled to RT and quenched with ice water. The solution was treated with NaHCO3 and NaCl, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN (3 mL) and the resulting solid was collected via filtration to afford 2-((2-methoxyethyl)amino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (65 mg, 61%). 1H NMR (400 MHz, DMSO-d6): δ 11.02 (br s, 1H), 8.67 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.29-8.23 (m, 2H), 7.96 (d, J=0.7 Hz, 1H), 7.50 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.85 (br s, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 3.53-3.44 (m, 4H), 3.28 (s, 3H), 2.34 (s, 3H); MS (ESI) m/z: 434.2 (M+H+).

Provenance & Evidence