Acetic Acid → HCID 59605466, compound

Participants

Reaction Steps

To a solution of 9-methyl-2-(2-methylbenzoimidazol-1-yl)-6-morpholin-4-yl-9H-purine-8-carbaldehyde (134 mg, 0.35 mmol) in DCE (5 mL) was added 7-azaspiro[3.5]nonan-2-ol (60 mg, 0.43 mmol), trimethyl orthoformate (0.19 mL, 1.77 mmol) and acetic acid (0.02 mL, 0.35 mmol). The reaction mixture was stirred at room temperature for 3 h, sodium triacetoxyborohydride (113 mg, 0.53 mmol) was added and the resulting mixture stirred for a further 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-20% MeOH in EtOAc) to give 343 as a white solid (80 mg, 45%). LCMS (Method G): RT=5.23 min, [M+H]+ 503.2. 1H NMR (400 MHz, CHCl3-d): δ 8.11-8.06 (m, 1 H), 7.73-7.68 (m, 1 H), 7.30-7.24 (m, 2 H), 4.37-4.24 (m, 4 H), 3.90-3.83 (m, 7 H), 3.72 (s, 2 H), 2.94 (s, 3 H), 2.58-2.31 (m, 4 H), 2.30-2.23 (m, 2 H), 1.75-1.55 (m, 8 H)

Provenance & Evidence