1-Hexyne → HCID 69538199, compound

HRID 2216264Notes

Reaction equation

I[C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH3:22])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH:24]#[C:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[C:24]([C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH3:22])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])#[C:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Reactant 2

HCID 127321-Hexyne

HCID 86592813HCID 86592813, compound

Product 1

HCID 69538199HCID 69538199, compound

Procedure

The reaction was performed with 2-iodo-8-ethylaminoadenosine (8, 67 mg, 0.15mmol) and 1-hexyn (0.73 mmol). The mixture was purified by column chromatography (EtOAc-10% MeOH in EtOAc). Yield 49 mg (0.12 mmol, 83%), mp230–232÷C; 1H NMR (DMSO-d6) δ 6.97 (t, 1H, J=4.80 Hz, NH), 6.57 (s, 2H, NH2), 5.86 (d, 1H, J=7.55 Hz, H-1′), 5.74 (t, 1H, J=4.80 Hz, OH-2′), 5.25 d, 1H, J=6.52 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.57 (q, 1H, J=6.18 Hz, H-2′), 4.08 (m, 1H, H-3′), 3.95 (m, 1H, H4′), 3.64–3.60 (m, 2H, H-5′), 3.05 (m, 2H, NHCH2), 2.36 (t, 2H, J=7.21 Hz, ≡CHCH2), 1.51–1.40 (m, 4H, CH2CH2CH3), 1.16 (t, 3H, J=7.20 Hz, NHCH2CH3), 0.89 (t, 3H, J=5.15 Hz, CH3); MS m/z 391 (M+H)+; Anal. (C18H26N6O4) C, H, N.

Workup

customThe mixture was purified by column chromatography (EtOAc-10% MeOH in EtOAc)

Sources & evidence

ORD record: ord-58c7739430274a678b8ebb87f4bc0af6
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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