Ammonia → N-[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethyl]-[1,3,5]triazine-2,4,6-triamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-N—[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[1,3,5]triazine-2,4-diamine (100 mg, 0.26 mmol) in dioxane (1 mL) was added 880 NH3 (4 mL). The reaction mixture was heated at 100° C. for 1 h using microwave irradiation. After cooling to RT, the reaction mixture was evaporated and purified by column chromatography (Si—PCC, gradient 2-12% 2M NH3/MeOH in DCM) affording 286 as a pink foam (72.9 mg, 77%). LCMS (Method K): RT 2.89 min [M+H]+ 365.0. 1H NMR (DMSO-d6, 400 MHz, 80° C.): δ 7.67-7.60 (3H, m), 7.57-7.51 (3H, m), 7.05 (1H, ddd, J=10.1, 8.8, 2.6 Hz), 6.78 (1H, dd, J=9.0, 2.5 Hz), 6.31 (1H, bd, J=7.5 Hz), 5.61 (4H, bs), 5.22 (1H, quintet, J=7.1 Hz), 1.40 (3H, d, J=6.9 Hz)

Provenance & Evidence