Diisopropylethylamine → HCID 178461699, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]methylamine (102 mg, 0.38 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (91 mg, 0.38 mmol) and DIPEA (0.33 mL, 1.9 mmol) in n-butanol (2 mL) was heated at 90° C. for 18 h in a sealed vial. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 181 (123 mg, 84%). LCMS (Method K): RT 3.39 min [M+H]+ 388.1. 1H NMR (DMSO-d6, 400 MHz, 80° C.): δ 7.99 (1H, s), 7.90 (1H, s), 7.75 (1H, dd, J=8.81, 4.87 Hz), 7.30-7.22 (2H, m), 7.17-6.95 (5H, m), 6.73 (1H, dd, J=8.93, 2.53 Hz), 3.12 (3H, br s), 1.71 (3H, d, J=6.76 Hz)

Provenance & Evidence