Methanol → HCID 24893959, compound

Participants

Reaction Steps

To a suspension of 5-(perylen-3-ylethynyl)-5′-O-pivaloyl-2′,3′-dideoxyuridine (350 mg, 0.613 mmol) in 80 mL of MeOH solid KOH (310 mg, 5.517 mmol) was added, and the mixture was stirred overnight. The mixture was then neutralized with acetic acid, evaporated under reduced pressure, co-evaporated with MeOH twice to give a crude product, which was chromatographically purified on a silica gel column using a 0 to 3% EtOH/CHCl3 gradient to give a chromatographically homogeneous (Rf 0.46, 37.5% acetone/CHCl3) product as orange solid (130 mg, 43%). 1H-NMR (DMSO-d6): 11.74 (s, 1H, NH), 8.76 (s, 1H, H-6), 8.45 (d, 1H, J 7.7), 8.41-8.38 (m, 2H), 8.36 (d, 1H, J 7.7), 8.30 (d, 1H, J 7.7), 7.71-7.54 (m, 6H) (perylenyl), 5.99-5.98 (m, 1H, H-1′), 5.35 (br. s, 1H, OH), 4.15-4.10 (m, 1H, H-4′), 3.70 (app. d, 1H, H-5′), 3.63 (app. d, 1H, H-5′), 2.38-2.31 (m, 1H, H-2′), 2.17-2.13 (m, 1H, H-2′), 2.01-1.94 (m, 1H, H-3′), 1.91-1.86 (m, 1H, H-3′).

Provenance & Evidence