Diisopropylethylamine → HCID 178463576, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethylamine (254 mg, 1.07 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.35 g, 1.49 mmol) and DIPEA (0.34 mL, 1.92 mmol) in 1-butanol (3 mL) was stirred at 90° C. in a sealed tube for 16 h. The resulting mixture was concentrated in vacuo and residue was purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM). The product was dissolved in methanol and treated with HCl/dioxane (4M, 1.3 mL, 5.35 mmol) and stirred for 20 minutes. The mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo. The resulting residue was purified by chromatography (SiO2, 0-15% (2M ammonia in methanol) in DCM) to give a waxy solid which was triturated with EtOAc/diethyl ether to give 237 as a brown solid (0.056 g, 15%). LCMS (method K): Rt 1.98 min, [M+H]+ 357. 1H NMR (DMSO-d6): δ 13.10-12.60 (1H, bs), 8.43 (1H, s), 8.37 (1H, d, J=5.53 Hz), 8.13 (1H, s), 8.07 (1H, s), 7.70-7.68 (3H, m), 7.61-7.50 (3H, m), 5.49 (1H, m), 1.59 (3H, d, J=6.87 Hz)

Provenance & Evidence