Sodium triacetoxyborohydride → HCID 59606165, compound

Participants

Reaction Steps

A solution of 9-methyl-2-(2-methylbenzoimidazol-1-yl)-6-morpholin-4-yl-9H-purine-8-carbaldehyde (100 mg, 0.27 mmol) and azetidin-3-ylpyrrolidin-1-ylmethanone (50 mg, 0.32 mmol) in DCE (3 mL) was stirred at ambient temperature for 90 min. Sodium triacetoxyborohydride (86 mg, 0.41 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, EtOAc:MeOH; gradient from 100:0 to 70:30) to afford 348 as a white foam (50 mg, 37%). LCMS (Method G): RT=5.81 min, M+H+=516. 1H NMR (CDCl3, 400 MHz) δ 8.08 (m, 1 H); 7.71 (m, 1 H); 7.26 (m, 2 H); 4.35 (m, 4 H); 3.89-3.83 (m, 9 H); 3.66 (m, 2 H); 3.55-3.43 (m, 5 H); 3.31 (m, 2 H); 2.94 (s, 3 H) and 1.98-1.81 (m, 4 H)

Provenance & Evidence