HCID 67492526, compound → HCID 59605854, compound

Participants

Reaction Steps

To a solution of 1-{3-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxyazetidin-1-yl}-2-hydroxyethanone (88 mg, 0.17 mmol) in THF (2 mL) at 0° C. was added BH3.THF complex (350 μL, 0.35 mmol, 1M solution) and the resulting mixture allowed to stir for 1 h. Further BH3.THF complex (800 μL, 0.80 mmol) was added and the mixture stirred at r.t. for 17 h. The reaction mixture was quenched with H2O, acidified with 2M HCl then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was dissolved in a mixture of MeCN and H2O and allowed to freeze-dry affording 849 as a white solid (74 mg, 86%). LCMS (method I): RT 2.48 min, [M+H]+ 493.4. 1H NMR (DMSO, 400 MHz): δ 8.04-8.04 (1 H, m), 7.64-7.63 (1 H, m), 7.27-7.23 (2 H, m), 4.50-4.42 (1 H, m), 4.39-4.14 (4 H, brd m), 4.05-3.98 (2 H, m), 3.80 (4 H, t, J=4.56 Hz), 3.70 (3 H, s), 3.52-3.45 (2 H, m), 3.40 (2 H, q, J=5.63 Hz), 3.34-3.24 (2 H, m), 3.01 (3 H, s), 2.65-2.57 (2 H, m), 1.34 (3 H, t, J=7.43 Hz)

Provenance & Evidence