1-Hexyne → HCID 69538223, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-methylaminoadenosine (7, 50 mg, 0.12 mmol) and 1-hexyn (0.58 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 36 mg (0.09 mmol, 79%), mp 161–163÷C; Rƒ 0.23 (5% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 7.01 (d, 1H, J=4.81 Hz, NH), 6.61 (s, 2H, NH2), 5.84 (d, 1H, J=7.55 Hz, H-1′), 5.78 (t, 1H, J=4.47 Hz, OH-2′), 5.26 (d, 1H, J=6.87 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.58 (q, 1H, J=5.83 Hz, H-2′), 4.10–4.03 (m, 1H, H-3′), 3.95 (bs, 1H, H-4′), 3.62 (bs, 2H, H-5′), 2.87 (s, 3H, J=4.46 Hz, NHCH3), 2.36 (t, 2H, J=6.87 Hz, ≡CCH2), 1.53–1.39 (m, 4H, CH2CH2), 0.89 (t, 3H, J=6.87 Hz, CH3); MS m/z 376 (M+H)+; Anal. (C17H24N6O4) C, H, N.

Provenance & Evidence