1-Hexyne → HCID 11442361, compound

HRID 2216267Notes

Reaction equation

I[C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[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:29]#[C:30][CH2:31][CH2:32][CH2:33][CH3:34]>>[C:29]([C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[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:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

Reactant 2

HCID 127321-Hexyne

HCID 86592816HCID 86592816, compound

Product 1

HCID 11442361HCID 11442361, compound

Procedure

The reaction was performed with 2-iodo-8-benzylaminoadenosine (11, 230 mg, 0.46 mmol) and 1-hexyn (2.23 mmol). The mixture was purified by column chromatography (EtOAc). Yield 146 mg (0.32 mmol, 70%), mp 141–143÷C; Rƒ 0.26 (5% MeOH in EtOAc); 1H NMR (DMSO-d6) δ 7.64 (t, 1H, J=6.10 Hz, NH), 7.36–7.18 (m, 5H, phenyl), 6.59 (bs, 2H, NH2), 5.92 (d, 1H, J=7.71 Hz, H-1′), 5.77 (t, 1H, J=4.85 Hz, OH-2′), 5.32 (d, 1H, J=6.74 Hz, OH-5′), 5.18 (d, 1H, J=4.18 Hz, OH-3′), 4.64 (q, 1H, J=4.64 Hz, H-2′), 4.58 (t, 2H, J=4.65 Hz, NHCH2), 4.09 (t, 1H, J=4.09 Hz, H-3′), 3.98 (d, 1H, J=1.60 Hz, H-4′), 3.62 (q, 2H, J=2.58 Hz, H-5′), 2.36 (t, 2H, J=6.92 Hz, ≡CCH2), 1.55–134 (m, 4H, CH2CH2), 0.89 (t, 3H, J=7.11 Hz, CH3); MS m/z 453 (M+H)+; Anal. (C23H28N6O4) C, H, N.

Workup

customThe mixture was purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-28690e544c73427c90adb6aaf9cd99a4
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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