Isobutylene oxide → HCID 59605246, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine (100 mg, 0.22 mmol) in MeCN (2 mL) was added 2,2-dimethyloxirane (198 μL, 2.23 mmol) and the resulting mixture stirred at 80° C. for 3 h before the addition of further 2,2-dimethyloxirane (1.0 mL, 11.15 mmol). The reaction mixture was stirred at 80° C. for a further 20 h then concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, MeOH:EtOAc, 0-20%) then triturated with Et2O and the resulting solid dried in vacuo affording 833 (31 mg, 27%). LCMS (method I): RT 2.59 min, [M+H]+ 521.3. 1H NMR (DMSO, 400 MHz): δ 8.04-8.04 (1 H, m), 7.66-7.62 (1 H, m), 7.25-7.24 (2 H, m), 4.29 (4 H, brd s), 4.07 (1 H, s), 3.99 (2 H, d, J=8.32 Hz), 3.80 (4 H, t, J=4.57 Hz), 3.70 (3 H, s), 3.52 (2 H, d, J=8.34 Hz), 3.34-3.19 (2 H, m), 3.02 (3 H, s), 2.43 (2 H, s), 1.34 (3 H, t, J=7.43 Hz), 1.05 (6 H, s)

Provenance & Evidence