Triethylamine → HCID 71589304, compound

Participants

Reaction Steps

A solution of 5-iodo-5′-O-pivaloyl-2′,3′-dideoxyuridine (442 mg, 1 mmol) and 3-perylenylacetylene (345 mg, 1.25 mmol) in 10 mL of DMF was degassed three times by alternation between vacuum and argon. Then Pd(PPh3)4 (115 mg, 0.1 mmol), CuI (38 mg, 0.2 mmol) and Et3N (0.278 mL, 2 mmol) were added and the flask was degassed once again, filled with argon, and the mixture was stirred for 43 hours at ambient temperature. The mixture was diluted with 300 mL of EtOAc, washed 3×200 mL of water, dried with Na2SO4, and evaporated. Chromatography on a silica gel column using a 0 to 2% of EtOH/CHCl3 gradient gave rise to a chromatographically homogeneous (Rf 0.28, 5% EtOH/CHCl3) product as orange foam (545 mg, 96%). 1H-NMR (DMSO-d6): 11.85 (s, 1H, NH), 8.44 (d, 1H, J 7.8), 8.39-8.35 (m, 3H), 8.32 (d, 1H, J 8.2) (perylenyl), 8.06 (s, 1H, H-6), 7.83-7.81 (m, 2H), 7.69-7.60 (m, 2H), 7.58-7.53 (m, 2H) (perylenyl), 6.00 (dd, 1H, J1′,2′α 6.9 J1′,2′β 4.6, H-1′), 4.37-4.34 (m, 1H, H-4′), 4.32-4.26 (m, 2H, H-5′), 2.42-2.36 (m, 1H, H-2′), 2.17-2.12 (m, 1H, H-2′), 2.06-2.00 (m, 1H, H-3′), 1.90-1.83 (m, 1H, H-3′), 1.17 (s, 9H, tBu).

Provenance & Evidence