1-Hexyne → HCID 9887483, compound

HRID 2216265Notes

Reaction equation

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

Participants

Reactant 2

HCID 127321-Hexyne

HCID 86592814HCID 86592814, compound

Product 1

HCID 9887483HCID 9887483, compound

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-9fe18a44da834a6c80c28d3c9d228bc6
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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