Sodium triacetoxyborohydride → HCID 59605390, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (162 mg, 0.41 mmol), 4-azetidin-3-yl-1-methylpiperazin-2-one (77 mg, 0.46 mmol) and 4 Å powdered molecular sieves (250 mg) in DCE (10 mL) was stirred at room temperature for 2 h before the addition of sodium triacetoxyborohydride (175 mg, 0.83 mmol). The reaction mixture was stirred for 16 h then filtered through celite, washing with DCM. The organic phase was washed with brine (×1) and concentrated in vacuo. The organic phase was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-30%) affording 556 as a yellow foam (182 mg, 82%). LCMS (Method I): RT 2.34 min [M+H]+ 545.3. 1H NMR (CDCl3, 400 MHz): δ 8.02-7.97 (m, 1 H); 7.77-7.72 (m, 1 H); 7.29-7.22 (m, 2 H); 4.35 (m, 4 H); 3.89-3.84 (m, 6 H); 3.83 (s, 3 H); 3.59 (t, J=5.3 Hz, 2 H); 3.39-3.31 (m, 4 H); 3.18-3.10 (m, 3 H); 3.05 (m, 2 H); 2.96 (s, 3 H); 2.59 (t, J=5.3 Hz, 2 H) and 1.43 (t, J=7.5 Hz, 3 H)

Provenance & Evidence