Trifluoroacetic acid → HCID 178519174, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 9-trityl-9H-purin-6-ylcarbamate (93 mg, 0.195 mmol) and 50% dispersion in mineral oil NaH (9.4 mg, 0.195 mmol) were dissolved in DMF (0.2 ml) at 0° C. A solution of 3-(bromomethyl)-4-(3-fluorophenyl)-1H-isochromen-1-one (intermediate C4, 50 mg, 0.150 mmol) in DMF (0.6 mL) was then added. The reaction mixture was stirred at 0° C. for 5 min and at RT for 15 min. The reaction mixture was then diluted with EtOAc (20 mL) and washed with 0.2 M HClaqueous, sat NaClaqueous dried over Na2SO4 and concentrated under reduced pressure to give the crude yellow oil. The crude was reacted with TFA (1.5 ml) in DCM (2 ml) for 1 hrs. Then it was diluted with DCM and dried under reduced pressure to give an yellow oil. This was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (20 mg, 34.4%) as colourless solid.

Provenance & Evidence