Hydrogen Bromide → HCID 86268247, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-N-neopentylpyrimidin-2-amine (0.081 g, 0.176 mmol) in acetic acid (2 mL) was treated with HBr (48% aq, 0.080 mL, 0.705 mmol), heated at 80° C. for 6 h, then cooled to RT overnight. The mixture was treated with ice and EtOAc, neutralized with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over MgSO4 and concentrated to dryness. The material was suspended in MeCN, heated to near-reflux and allowed to stand at RT for 3 h. The resulting solid was collected via filtration to afford 5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(neopentylamino)pyrimidin-4(3H)-one (44 mg, 56%). 1H NMR (400 MHz, DMSO-d6): δ 10.84 (s, 1H), 8.68 (s, 1H), 8.35 (d, J=6.6 Hz, 1H), 8.28-8.23 (m, 2H), 7.96 (s, 1H), 7.52 (d, J=8.6 Hz, 1H), 7.22 (d, J=3.0 Hz, 1H), 6.73 (br s, 1H), 6.60 (dd, J=5.1, 2.3 Hz, 1H), 3.86 (s, 3H), 3.22 (d, J=6.2 Hz, 2H), 2.34 (s, 3H), 0.91 (s, 9H); MS (ESI) m/z: 446.2 (M+H+).

Provenance & Evidence