Diisopropylethylamine → HCID 178461958, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(3-pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (0.134 g, 0.56 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.186 g, 0.78 mmol) and DIPEA (0.18 mL, 1.01 mmol) in IPA (2 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, 1.0 mL, 4.00 mol) and stirred for 30 min. The resulting mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo to give 293 as a white solid (0.160 g, 80%). LCMS (method K): Rt 2.28 min, [M+H]+ 358. 1H NMR (DMSO-d6): δ 13.20-12.70 (1H, bs), 8.59 (1H, s), 8.31 (1H, m), 8.13 (2H, m), 8.03 (2H, tm), 7.81-7.81 (1H, m), 7.47 (1H, s), 7.36 (1H, m), 5.99 (1H, m), 1.67 (3H, d, J=6.82 Hz)

Provenance & Evidence