Triethylamine → HCID 86684719, compound

Participants

Reaction Steps

A solution of compound 61 (80 mg, 0.13 mmol), N-propargyltrifluoroacetylamide (196 mg, 1.30 mmol), tetrakis(triphenylphosphine)-palladium(0) (30 mg, 0.026 mmol), CuI (9.9 mg, 0.052 mmol), and Et3N (80 μL) in anhydrous DMF (3.0 mL) was stirred at 50° C. for 12 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to yield 5-{(S)-1-[5-methoxy-4-(3-trifluoroacetamido-1-propynyl)-2-nitrophenyl]-2,2-dimethyl-propyloxy}methyl-2′-deoxyuridine 62 (75 mg, 90%). 1H NMR (400 MHz, MeOD-d4): δ 8.11 (s, 1H, H-6), 8.08 (s, 1H, Ph-H), 7.36 (s, 1H, Ph-H), 6.27 (t, 1H, J=6.4 Hz, H-1′), 5.33 (s, 1H, Ph-CH), 4.47 (m, 1H, H-3′), 4.44 (s, 2H, 5-CH2), 4.32 (d, 2H, J=2.0 Hz, CH2), 4.08 (s, 3H, OCH3), 3.99 (m, 1H, H-4′), 3.87 (m, 1H, H-5′a), 3.79 (m, 1H, H-5′b), 2.30 (m, 2H, H-2), 0.93 (s, 9H, C(CH3)3).

Provenance & Evidence