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

Participants

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 EtOAc (10 mL) was added a slurry of 10% Pd/C (40 mg) in IMS (5 mL) and the reaction mixture stirred at RT under a hydrogen atmosphere for 18 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (C18, gradient 20-55% MeOH in 0.5% TFA/H2O) then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH affording 267 as a colourless foam (42.3 g, 46%). LCMS (Method K): RT 3.14 min [M+H]+ 350.0. 1H NMR (DMSO-d6, 400 MHz, 80° C.): δ 7.87 (1H, s), 7.66 (1H, dd, J=8.8, 4.9 Hz), 7.60-7.56 (2H, m), 7.54-7.49 (3H, m), 7.08 (1H, bs), 7.04 (1H, ddd, J=9.8, 8.7, 2.5 Hz), 6.77 (1H, dd, J=9.0, 2.5 Hz), 6.28 (2H, bs), 5.23 (1H, quintet, J=7.1 Hz), 1.45 (3H, d, J=6.9 Hz)

Provenance & Evidence