(3S)-N,N-dimethylpyrrolidine-3-carboxamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (100 mg, 0.26 mmol) and (S)-pyrrolidine-3-carboxylic acid dimethylamide (44 mg, 0.31 mmol) in DCE (5 mL) was stirred at ambient temperature for 4 h. Sodium triacetoxyborohydride (81 mg, 0.38 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 398 as a cream solid (50 mg, 38%). LCMS (Method G): RT=5.90 min, M+H+=518. 1H NMR (CDCl3, 400 MHz) δ 8.01 (m, 1 H); 7.75 (m, 1 H); 7.28 (m, 2 H); 4.35 (m, 4 H); 3.98-3.80 (m, 9 H); 3.40-3.25 (m, 3 H); 3.20-2.78 (m, 10 H); 2.15-2.07 (m, 2 H) and 1.50-1.41 (m, 3H) The cartridge was then washed with methanol the desired product was subsequently eluted The product was collected concentrated in vacuo The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; gradient from 100:0 to 70:30)