Acetone → 4-(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-8-(1-isopropyl-3-methoxyazetidin-3-yl)-9-methyl-9H-purin-6-yl)morpholine

Participants

Reaction Steps

To a solution of 2-(2-ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine (553 mg, 1.23 mmol) and propan-2-one (1.0 mL) in MeOH (20 mL) was added 10% Pd/C (30 mg) as a slurry in MeOH (0.5 mL) and the resulting mixture stirred under an atmosphere of H2 for 1.5 h at r.t. The reaction mixture was filtered through Celite®, washing with MeOH, and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, 2M NH3/MeOH:EtOAc, 0-12%) then (C18, MeOH:H2O, 5-25%). The resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with DCM and MeOH and the product eluted with 2M NH3/MeOH. The resulting colourless foam was recrystallised from iPrOAc and pentane affording 739 as colourless crystals (166 mg, 28%). LCMS (method I): RT 2.48 min, [M+H]+ 491.3. 1H NMR (CDCl3, 400 MHz): δ 8.03-8.02 (1 H, m), 7.64-7.63 (1 H, m), 7.29-7.28 (2 H, m), 4.40 (4 H, s), 4.05 (2 H, d, J=8.89 Hz), 3.86 (4 H, s), 3.81 (3 H, s), 3.57-3.55 (2 H, m), 3.31-3.30 (2 H, m), 3.10 (3 H, s), 2.54-2.53 (1 H, m), 1.40 (3 H, t, J=7.50 Hz), 1.02 (6 H, d, J=6.24 Hz)

Provenance & Evidence