Sodium hydride → 2-[1-(2-aminopyrimidin-4-yl)-6-iodo-1H-indazol-3-yl]propan-2-ol

Participants

Reaction Steps

To a solution of 2-(6-iodo-1H-indazol-3-yl)propan-2-ol (1.00 g, 3.31 mmol) in dry DMF (30 mL) at 0° C. under an atmosphere of nitrogen was introduced sodium hydride (212 mg of a 60% dispersion in mineral oil, 5.3 mmol). After 20 minutes at this temperature, 4-chloropyrimidin-2-amine (858 mg, 6.62 mmol) was added and the solution warmed to RT for 10 minutes, then to 65° C. for 23 hr. The reaction mixture was cooled to RT, quenched carefully with water (20 mL) and extracted with EtOAc (2×20 mL extractions). The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography (4:1 to 1:1 heptane/EtOAc gradient) furnished the title compound as an off-white solid: 1H NMR (250 MHz, CDCl3) delta 1.73-1.83 (6H, m), 2.77 (1H, s), 5.16 (2H, s), 7.23-7.33 (1H, m), 7.55-7.64 (1H, m), 7.68-7.78 (1H, m), 8.30 (1H, d, J=5.79 Hz), 9.15-9.28 (1 H, m); LC-MS: m/z=+395.90 (M+H)+.

Provenance & Evidence