Trifluoroacetic acid → HCID 136247206, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-(trifluoromethyl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (47.7 mg, 116 μmol) in anhydrous methylene chloride (6.0 mL) was cooled, under nitrogen, to 0° C. The solution was then treated portion-wise with trifluoroacetic acid (1.5 mL). The reaction was stirred under nitrogen at 0° C. for 30 min. At this time, the reaction was warmed to room temperature where it continued to stir for an additional 3 h. At this time, the reaction was diluted with methylene chloride and was concentrated in vacuo onto Celite® while maintaining a water bath temperature less than or equal to 30° C. Flash chromatography (12 g silica gel column, 40-70% ethyl acetate/hexanes) afforded 7-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as an off-white solid (20.9 mg, 58.0%). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.55 (d, J=7.91 Hz, 2H) 6.56 (d, J=3.39 Hz, 1H) 6.63 (t, J=7.35 Hz, 1H) 7.27 (d, J=3.39 Hz, 1H) 7.91 (d, J=8.48 Hz, 2H) 8.37 (d, J=8.10 Hz, 2H) 12.38 (s, 1H). LC-MS calcd. for C14H11F3N3O2 [(M+H)+] 310, obsd. 310.0.

Provenance & Evidence