Diisopropylethylamine → HCID 178463577, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)ethylamine (184 mg, 0.77 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (256 mg, 1.08 mmol) and DIPEA (0.25 mL, 1.39 mmol) in 1-butanol (2 mL) was stirred at 90° C. in a sealed microwave tube for 16 h. The resulting mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH. The product was eluted with 2M NH3/MeOH then concentrated in vacuo. The resulting residue was purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM), then by preparative HPLC (Phenomenex Gemini 5 μm C18 on a 60 min gradient 20-98% 0.1% HCO2H in acetonitrile/water) to give 236 as a white solid (0.017 g, 6%). LCMS (method K): Rt 2.04 min, [M+H]+ 357. 1H NMR (DMSO-d6): δ 12.89 (1H, s), 8.94 (1H, s), 8.30 (1H, d, J=5.54 Hz), 8.09-8.00 (2H, m), 7.65-7.50 (5H, m), 7.12 (1H, d, J=5.57 Hz), 5.53 (1H, s), 1.58 (4H, d, J=7.36 Hz)

Provenance & Evidence