N-(2-amino-4-(tert-butyl)phenyl)-2-(3-((((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)(methyl)amino)cyclobutyl)acetamide → HCID 178491019, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-amino-4-(tert-butyl)phenyl)-2-(3-((((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)(methyl)amino)cyclobutyl)acetamide (272 mg, 0.374 mmol) was taken up in acetic acid (7.2 mL) and the solution was heated at 65° C. After 1.5 h, HPLC indicated the reaction was complete. The reaction was cooled to room temperature and the solvent removed under high vac. The residue was taken up in 35 mL CH2Cl2 and the organic phase was washed with 25 mL sat NaHCO3 solution and 20 mL 2% Na2CO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light tan glass/stiff foam. The crude material was purified by flash chromatography (30 g silica gel; 4% 7N NH3 in CH3OH/CH2Cl2) to yield the title compound (224 mg, 84%) as a light tan glass which was a mixture of cis and trans diastereomers about the cyclobutyl ring: MS (ESI+) for C40H51N7O5 m/z 710.6 (M+H)+; MS (ESI−) for C41H51N7O5 m/z 708.7 (M−H)−; HPLC purity >95% (ret. time, 3.29, 3.33 min), two peaks observed due to diastereomers about the cyclobutyl ring.

Provenance & Evidence