(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → (2R)-4-[1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(6-bromo-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine (160 mg, 0.52 mmol) in piperidine (2 mL) was introduced tetrakis(triphenylphosphine)palladium(0) (60.59 mg, 0.05 mmol), copper(I) iodide (9.99 mg, 0.05 mmol) and (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (118.9 mg, 0.79 mmol). The reaction was then warmed to 95° C. for 40 minutes (75 W, microwave heating). The reaction mixture was then cooled to RT and concentrated in vacuo. Purification of the residue by flash column chromatography (4-8% MeOH gradient in DCM) gave the title compound as a pale brown solid (77 mg): 1H NMR (500 MHz, DMSO) delta 1.81 (3H, s), 2.41 (3H, s), 2.90 (3H, s), 6.37 (1H, s), 6.51 (1H, s), 7.33 (1H, dd, J=8.28, 1.50 Hz), 7.60 (1H, d, J=8.20 Hz), 8.01 (1H, br. s.), 8.06 (1H, br. s.), 8.40 (1H, s), 8.66 (1H, s); LC-MS: m/z=+376.45 (M+H)+.

Provenance & Evidence