Diisopropylethylamine → HCID 178461944, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(1-benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine (322 mg, 1.20 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (286 mg, 1.20 mmol) and DIPEA (1.07 mL, 5.98 mmol) in IPA (5 mL) was heated at 90° C. in a sealed vial overnight. The resultant mixture was allowed to cool to RT and then concentrated in vacuo. The residue was passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and 2M NH3 in MeOH solution to afford a pale red gum. This was purified by column chromatography (silica gel, gradient 0-10% [2M NH3 in MeOH] in DCM) to afford 393 as a white solid (140 mg, 31%). LCMS (Method K): RT 3.21 min [M+H]+ 388.1 1H NMR (DMSO-d6, 400 MHz): δ 8.20 (1H, s), 8.13 (1H, s), 8.04-7.93 (1H, s), 7.63 (1H, dd, J=8.80, 4.92 Hz), 7.35-7.17 (4H, m), 7.16-7.10 (2H, m), 7.03 (1H, ddd, J=9.91, 8.78, 2.52 Hz), 5.93-5.75 (1H, m), 5.61 (2H, s), 1.59 (3H, d, J=6.77 Hz)

Provenance & Evidence