1-Hexyne → HCID 69538203, compound

HRID 2216266Notes

Reaction equation

I[C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[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:26]#[C:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[C:26]([C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[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:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

Reactant 2

HCID 127321-Hexyne

HCID 86592815HCID 86592815, compound

Product 1

HCID 69538203HCID 69538203, compound

Procedure

The reaction was performed with 2-iodo-8-butylaminoadenosine (10, 200 mg, 0.43 mmol) and 1-hexyn (2.08 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 111 mg (0.26 mmol, 62%), mp 182–184÷C; 1H NMR (DMSO-d6) δ 6.95 (t, 1H, J=5.49 Hz, NH), 6.55 (bs, 2H, NH2), 5.87 (d, 1H, J=7.90 Hz, H-1′), 5.77–5.72 (m, 1H, OH-2′), 5.26 (d, 1H, J=6.52 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.54 (q, 1H, J=5.84 Hz, H-2′), 4.09–4.04 (m, 1H, H-3′), 3.95–3.93 (m, 1H, H-4′), 3.64–3.59 (m, 2H, H-5′), 3.09 (m, 2H, NHCH2), 2.36 (m, 2H, ≡CCH2), 1.51–1.30 (m, 8H, 2×CH2CH2), 0.89 (t, 6H, J=,7.55 Hz, 2×CH3); MS m/z 419 (M+H)+; Anal. (C20H30N6O4) C, H, N.

Workup

customThe mixture was purified by column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-ced13e6804f346df89e088d263b2ab3f
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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