Sodium triacetoxyborohydride → HCID 67492361, compound

Participants

Reaction Steps

A solution of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (100 mg, 0.26 mmol) and pyrrolidin-1-yl-(S)-pyrrolidin-3-ylmethanone (51 mg, 0.30 mmol) in DCE (5 mL) was stirred at ambient temperature for 2 h. Sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added and the mixture stirred for 18 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, DCM:MeOH; gradient from 100:0 to 70:30) to afford 399 as a white solid (132 mg, 86%). LCMS (Method G): RT=6.43 min, M+H+=544. 1H NMR (CDCl3, 400 MHz) δ 7.99 (m, 1 H); 7.75 (m, 1 H); 7.27 (m, 2 H); 4.35 (m, 4 H); 3.94 (s, 2 H); 3.87 (m, 7 H); 3.50-3.38 (m, 4 H); 3.35 (q, J=7.5 Hz, 2 H); 3.20-3.10 (m, 1 H); 3.01 (m, 1 H); 2.87 (m, 2 H); 2.72 (m, 1 H); 2.16-2.07 (m, 2 H); 2.01-1.90 (m, 2 H); 1.91-1.81 (m, 2 H) and 1.45 (t, J=7.5 Hz, 3 H)

Provenance & Evidence