Sodium triacetoxyborohydride → HCID 59605807, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (100 mg, 0.26 mmol), 1-oxa-4,9-diazaspiro[5.5]undecan-3-one (61 mg, 0.36 mmol) and molecular sieves (4 Å, powdered, 255 mg) in DCE (5 mL) was stirred at ambient temperature for 1 h. Sodium triacetoxyborohydride (81 mg, 0.38 mmol) was added and the mixture stirred for 17 h, then loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, EtOAc:MeOH; gradient from 100:0 to 70:30) to afford 394 as a cream solid (116 mg, 83%). LCMS (Method G): RT=5.76 min, M+H+=546. 1H NMR (CDCl3, 400 MHz) δ 8.01 (m, 1 H); 7.77 (m, 1 H); 7.32-7.24 (m, 2 H); 5.93 (bs, 1 H); 4.35 (m, 4 H); 4.18 (s, 2 H); 3.90-3.84 (m, 7 H); 3.82 (bs, 2 H); 3.37 (q, J=7.5 Hz, 2 H); 3.27 (m, 2 H); 2.72 (m, 2 H); 2.59 (m, 2 H); 2.05-1.93 (m, 2 H); 1.68 (m, 2 H) and 1.46 (t, J=7.5 Hz, 3 H)

Provenance & Evidence