Sodium Iodide → 2-(4-(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)piperidin-1-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-8-piperidin-4-yl-9H-purine hydrochloride (150 mg, 0.31 mmol), 2-bromoacetamide (45 mg, 0.33 mmol), sodium iodide (5 mg, 0.03 mmol) and K2CO3 (90 mg, 0.65 mmol) in MeCN (3 mL) was heated to 50° C. for 2 h in a sealed tube. The reaction mixture was diluted with EtOAc, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-30%) affording 677 (119 mg, 76%). LCMS (method I): RT 2.40 min, [M+H]+ 504.2. 1H NMR (DMSO, 400 MHz): δ 8.02-7.98 (1 H, m), 7.64-7.63 (1 H, m), 7.25-7.24 (4 H, m), 4.27 (4 H, brd s), 3.82-3.72 (7 H, m), 3.35-3.30 (2 H, m), 3.26 (2 H, q, J=7.45 Hz), 3.11-2.90 (4 H, m), 2.38-2.31 (1 H, m), 1.97 (4 H, s), 1.33 (3 H, t, J=7.44 Hz)

Provenance & Evidence