Diisopropylethylamine → HCID 178461930, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-(1-Cyclohexyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine (0.41 g, 1.56 mmol) was dissolved in n-butanol (5 mL) and 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.374 g, 1.56 mmol) and DIPEA (1.38 mL, 7.82 mmol) added. The reaction mixture was heated to 100° C. overnight. The resultant mixture was allowed to cool to RT and was concentrated in vacuo. The residue was passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and 2M NH3 in MeOH to afford crude product. This was purified by column chromatography (silica gel, gradient 0-10% MeOH in DCM) to afford 201 as a pale yellow gum, which solidified on standing (204 mg, 35%). LCMS (Method K): RT 3.31 min [M+H]+ 380.1 1H NMR (DMSO-d6, 400 MHz): δ 8.30 (1H, s), 8.15 (1H, s), 8.04 (1H, s), 7.66-7.54 (2H, m), 7.02 (1H, td, J=9.29, 2.34 Hz), 6.00 (1H, s), 4.51-4.37 (1H, m), 2.27-2.13 (1H, m), 2.07-1.95 (1H, m), 1.88-1.75 (2H, m), 1.70 (3H, d, J=6.70 Hz), 1.64-1.44 (3H, m), 1.39-1.26 (2H, m), 0.75-0.57 (1H, m)

Provenance & Evidence