5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-amine → N-(5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide

Participants

Reaction Steps

A 0° C. solution of Example B2 (0.14 g, 0.60 mmol) in DCM (3 mL) was treated drop-wise with a solution of 5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-amine (0.08 g, 0.30 mmol) and TEA (0.1 mL, 0.9 mmol) in DCM (2 mL), warmed to RT and stirred for 2 h. The mixture was concentrated to dryness, purified via silica gel chromatography (MeOH/DCM), treated with Et2O and the resulting solid collected via filtration to afford N-(5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (93 mg, 67%). 1H NMR (400 MHz, DMSO-d6): δ 10.94 (s, 1 H), 8.62 (d, J=1.1 Hz, 1 H), 8.46 (s, 1 H), 8.22 (m, 1 H), 8.16 (d, J=0.7 Hz, 1 H), 8.04 (d, J=9.0 Hz, 1 H), 7.74 (dd, J=9.0, 2.9 Hz, 1 H), 7.42 (d, J=1.1 Hz, 1 H), 3.89 (s, 3 H), 4.00-3.70 (m, 5 H), 3.42-3.39 (m, 4 H), 1.76-1.65 (m, 2 H), 1.59 (m, 2 H); MS (ESI) m/z: 465.2 (M+H+).

Provenance & Evidence