1-Ethynylcyclohexanol → Gne-2861

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine (150 mg, 0.39 mmol, 95%), triethylamine (2 mL), 1-ethynylcyclohexan-1-ol (300 mg, 2.42 mmol) and bis(triphenylphosphine)palladium(II) dichloride (300 mg, 0.43 mmol) in dimethylsulfoxide (3 mL) was stirred under nitrogen for 1 hr at 70° C. The reaction mixture was purified on a C18 column (acetonitrile/water, 5:95-80:20) to give 30 mg (19%) of 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol as a white solid: 1H NMR (300 MHz, DMSO) delta 8.43 (d, J=5.4 Hz, 1H), 8.22 (d, J=5.4 Hz, 1H), 7.50 (s, 1H), 7.30-7.10 (m, 4H), 6.91 (s, 1H), 5.33 (s, 1H), 4.69-4.55 (m, 4H), 3.30 (s, 3H), 1.90-1.20 (m, 10H); LC-MS: m/z=407 (M+H)+.

Provenance & Evidence