2-(Di-tert-butylphosphino)biphenyl → N-methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}urea

Participants

Reaction Conditions

Reaction Steps

A solution of 5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride (26 mg, 0.1 mmol), N-(4-bromophenyl)-N-methylurea (27 mg, 0.12 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.01 mmol), 2-(di-t-butylphosphino)biphenyl (10 mg, 0.03 mmol) and sodium t-butoxide (25 mg, 0.23 mmol) in dioxane (0.80 mL) was added to a Smithcreator microwave reaction vessal. The vessal was sealed, then heated in the Smithcreator microwave at 160° C. for 20 minutes. After cooling to room temperature, the mixture was purified by silica gel chromatography, eluting with 5% MeOH/DCM to give N-methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}urea (14 mg, 38%) as a yellow solid. 1H NMR (DMSO-d6): δ9.59 (s, 1H), 9.20 (s, 1H), 8.39-8.46 (m, 3H), 7.34-7.71 (m, 8H), 5.94 (d, J=4.67 Hz, 1H), 2.63 (d, J=4.53 Hz, 3H), 2.52 (s, 3H). MS m/z 373 (M+1).

Provenance & Evidence