Triethylamine → HCID 60163744, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[6-bromo-2-[(pyrrolidin-1-yl)carbonyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (200 mg, 0.49 mmol), 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (200 mg, 1.32 mmol), bis(triphenylphosphine)palladium(II) dichloride (350 mg, 0.50 mmol) and triethylamine (2 mL) in dimethylsulfoxide (3 mL) was stirred under nitrogen at 70° C. for 2 hr. The reaction mixture was cooled to room temperature and purified on a C18 column (acetonitrile/water, 5:95-80:20) to afford 88 mg (38%) of 4-[1-(2-aminopyrimidin-4-yl)-2-[(pyrrolidin-1-yl)carbonyl]-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol as a light yellow solid. 1H NMR (300 MHz, DMSO) delta 8.42 (d, J=5.1 Hz, 1H), 7.86 (s, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.03 (s, 2H), 6.74 (d, J=5.1 Hz, 1H), 6.50 (s, 1H), 6.36 (s, 1H), 3.61 (d, J=6.6 Hz, 2H), 3.48 (d, J=6.6 Hz, 2H), 2.40 (s, 3H), 1.92 (s, 4H), 1.80 (s, 3H); LC-MS: m/z=+458 (M+H)+.

Provenance & Evidence