1-Tert-butyl-4-isocyanatobenzene → HCID 67818966, compound

Participants

Reaction Steps

A suspension of N1-(((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)-N1-isopropylpropane-1,3-diamine (1.11 g, 2.00 mmol, crude from step 6) in methylene chloride (40 mL) was treated dropwise with a solution of 1-tert-butyl-4-isocyanatobenzene (0.36 mL, 2.0 mmol) in methylene chloride (3.5 mL) and allowed to stir at room temperature. After 1 h, reaction was complete by HPLC. The reaction mixture was concentrated to yield a glass. The crude material was purified by flash chromatography (100 g silica gel, 2-4% 7N NH3 in CH3OH/CH2Cl2 to yield the title compound (1.07 g, 73%) as a foam: MS (ESI+) for C40H55N7O6 m/z 730.4 (M+H)+; (ESI−) for C40H55N7O6 m/z 728.5 (M−H)−; HPLC purity, 89% (ret. time, 3.78 min).

Provenance & Evidence