p-Toluenesulfonic acid → 4-(8-((4-tert-butylpiperazin-1-yl)methyl)-2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

Into a vial was added 4-(8-((4-tert-butylpiperazin-1-yl)methyl)-2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholine (126 mg, 0.264 mmol), 2-ethyl-1H-benzo[d]imidazole (40.4 mg, 0.277 mmol), Xphos (16.3 mg, 0.0343 mmol), tris(dibenzylideneacetone)dipalladium(0) (16.4 mg, 0.0179 mmol), and cesium carbonate (172 mg, 0.527 mmol;). The mixture was dissolved in N,N-dimethylformamide (2.02 mL, 0.0261 mol) and heated at 145° C. under pressure for 30 minutes in a microwave reactor. The reaction mixture was filtered and concentrated. The crude residue was dissolved in MeOH (5.0 mL) and para-toluenesulfonic acid (90.8 mg, 0.527 mmol) was added. The reaction was heated overnight at 40° C. The reaction mixture was concentrated to dryness and purified by reverse phase HPLC to give 401 (50.9 mg, 38.3%). [M+H]+=504.3

Provenance & Evidence