Diisopropylethylamine → HCID 67818475, compound

Participants

Reaction Steps

A solution of 5-((((3aR,4R,6R,6aR)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)pentanoic acid (131 mg, 0.219 mmol) and 4-tert-butylbenzene-1,2-diamine (40 mg, 0.24 mmol) in N,N-dimethylformamide (2.2 mL) was treated with N,N-diisopropylethylamine (84 uL, 0.48 mmol) dropwise followed by PyBop reagent (120 mg, 0.24 mmol). The solution was allowed to stir at room temperature for 19 h, whereupon HPLC indicated the reaction was complete. The reaction mixture was concentrated under high vacuum. The residue was taken up in 40 mL CH2Cl2 and washed with 20 mL portions of H2O, 5% citric acid, and brine. The organic phase was dried over Na2SO4, filtered and concentrated to yield a tan viscous glass. The crude material was purified by flash chromatography (40 g silica gel; 2% 7N NH3 in CH3OH/CH2Cl2 to yield the title compound (140 mg, 86%) was a slightly tan glass: MS (ESI+) for C41H57N7O6 m/z 744.9 (M+H)+; HPLC purity (combined for the two regioisomers) 91% (ret. times, 3.25 and 3.28 min).

Provenance & Evidence