4-{6-Iodo-3-[(morpholin-4-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine → (2S)-4-[1-(2-aminopyrimidin-4-yl)-3-[(morpholin-4-yl)carbonyl]-1H-indazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

Participants

Reaction Steps

To solution of 4-{6-iodo-3-[(morpholin-4-yl)carbonyl]-1H-indazol-1-yl}pyrimidin-2-amine (60 mg, 0.13 mmol) in triethylamine (2 mL) was introduced tetrakis(triphenylphosphine)palladium (0) (15.4 mg, 0.01 mmol), copper(I) iodide (2.5 mg, 0.01 mmol) and (2S)-2-(pyrimidin-2-yl)but-3-yn-2-ol (30 mg, 0.20 mmol). After 18 hr at RT, the reaction mixture was concentrated in vacuo, DCM (10 mL) was added and the solution re-evaporated to dryness in vacuo (re-evaporation process repeated twice). Purification of the residue by column chromatography (Biotage, DCM containing a 0-10% gradient of methanol) furnished the title compound as an off-white solid: 1H NMR (500 MHz, DMSO-d6) delta 1.79-2.05 (3H, m), 3.59-3.68 (2H, m), 3.71-3.79 (4H, m), 3.89-4.01 (2H, m), 6.17-6.37 (1H, m), 6.98-7.10 (1H, m), 7.12-7.27 (2H, m), 7.32-7.42 (1H, m), 7.47-7.58 (1H, m), 7.92-8.05 (1H, m), 8.26-8.39 (1H, m), 8.80-9.04 (3H, m); LC-MS: m/z=+471.05 (M+H)+.

Provenance & Evidence