1-Hexyne → HCID 9887483, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-propylaminoadenosine (9, 68 mg, 0.15 mmol) and 1-hexyn (0.73 mmol). The mixture was purified by column chromatography (EtOAc-10% MeOH in EtOAc). Yield 49 mg (0.12 mmol, 80%), mp 184–186÷C; Rƒ 0.60 (10% MeOH in EtOAc); 1H NMR (DMSO-d6) δ 6.98 (t, 1H, J=5.15 Hz, NH), 6.54 (bs, 2H, NH2), 5.87 (d, 1H, J=7.55 Hz, H-1′), 5.75 (t, 1H, J=4.46 Hz, OH-2′), 5.26 (d, 1H, J=6.86 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.55 (q, 1H, J=6.86 Hz, H-2′), 4.06 (m, 1H, H-3′), 3.96 (bs, 1H, H4′), 3.61 (bs, 2H, H-5′), 2.49 (m, 2H, NHCH2), 2.36 (m, 2H, ≡CCH2), 1.60–1.42 (m, 6H, NHCH2CH2CH3, CH2CH2), 0.89 (t, 6H, J=7.55 Hz, 2×CH3); MS m/z 405 (M+H)+; Anal. (C19H28N6O4) C, H, N.

Provenance & Evidence