Trifluoroacetic acid → HCID 86723445, compound

Participants

Reaction Steps

To a stirred solution of S-(1-((tert-butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate (step 4) (1.62 g, 3.23 mmol) in EtOH (25 ml) was added sodium borohydride (0.61 g, 16.14 mmol) at 0° C. and the solution stirred overnight at RT. The reaction mixture was added slowly to TFA in water (20 ml, 50%). The resulting solid was removed by filtration and the filtrate was concentrated in vacuo to remove EtOH. The resulting mixture was diluted with water and extracted with DCM (×3). The combined organic extracts were passed through a hydrophobic frit and concentrated under reduced pressure to afford an oil. The oil was dissolved in a minimal volume of DCM and purified via ISCO column chromatography, 12 g, liquid load, 0-90% EtOAc in iso-hexane to afford the title compound;

Provenance & Evidence