Diisopropylethylamine → HCID 178456071, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propylamine (430 mg, 1.70 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (560 mg, 2.39 mmol) and DIPEA (0.54 mL, 3.07 mmol) in n-butanol (3 mL) was heated at 90° C. in a sealed vial for 16 h. After cooling to RT, the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) to afford 169 as a white solid (136 mg, 22%). LCMS (Method K): RT 2.89 min [M+H]+ 371.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.91 (1H, s), 8.30-7.70 (5H, m), 7.68-7.21 (6H, m), 5.42 (1H, s), 2.01 (2H, bs), 1.01-0.71 (3H, m).

Provenance & Evidence