Hydrogen Bromide → HCID 86270438, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methoxy-N,N-dimethyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.060 g, 0.144 mmol) in acetic acid (5 mL) was treated with HBr (0.065 mL, 0.575 mmol), heated at 90° C. for 6 h, cooled to RT and quenched with ice water. The solution was treated with NaHCO3 and NaCl, extracted with 1:1 THF/EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN (1 mL), allowed to stand at RT and the resulting solid was collected via filtration to afford 2-(dimethylamino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (43 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 8.73 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.30 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.51 (m, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.62 (br s, 1H), 3.85 (s, 3H), 3.12 (s, 6H), 2.35 (s, 3H); MS (ESI) m/z: 404.2 (M+H+).

Provenance & Evidence