1-Hexyne → HCID 86592816, compound

HRID 2216262Notes

Reaction equation

[C:1]([C:7]1[N:8]=C(N)C2N=CN(C=2N=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[I:26][C:27]1[N:28]=[C:29]([NH2:45])[C:30]2[N:31]=[CH:32][N:33]([C:43]=2[N:44]=1)[C@@H:34]1[O:42][C@H:39]([CH2:40][OH:41])[C@@H:37]([OH:38])[C@H:35]1[OH:36].C#CCCCC>>[I:26][C:27]1[N:28]=[C:29]([NH2:45])[C:30]2[N:31]=[C:32]([NH:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:33]([C:43]=2[N:44]=1)[C@@H:34]1[O:42][C@H:39]([CH2:40][OH:41])[C@@H:37]([OH:38])[C@H:35]1[OH:36]

Participants

Reactant 3

HCID 127321-Hexyne

HCID 1696622-Iodoadenosine

HCID 10020580HCID 10020580, compound

Product 1

HCID 86592816HCID 86592816, compound

Procedure

2-(1-hexynyl)adenosine (Compound 3).8 The reaction was performed with 2-iodoadenosine (1, 255 mg, 0.65 mmol) and 1-hexyn (3.15 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 192 mg (0.55 mmol, 85%), mp 106–109÷C; Rƒ 0.10 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.37 (s, 1H, H-8), 7.41 (bs, 2H, NH2), 5.84 (d, J=6.18 Hz, 1H, H-1′), 5.45 (d, J=6.18 Hz, 1H, OH-2′), 5.22–5.16 (m, 1H, OH-5′), 5.22–5.16 (m, 1H, OH-3′), 4.52 (q, J=5.15 Hz, 1H, H-2′), 4.11 (q, J=3.43 Hz, 1H, H-3′), 3.93 (pd, J=3.43 Hz, 1H, H4′), 3.65–3.48 (m, 2H, H-5′), 2.39 (t, J=6.86 Hz, 2H, ≡CCH2), 1.51–1.39 (m, 4H, CH2CH2), 0.90 (t, J=6.87 Hz, 3H, CH3); MS m/z 348 (M+H)+; Anal. (C16H21N5O4 0.22 CH2Cl2) C, H, N.

Workup

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

Sources & evidence

ORD record: ord-7e50896d969748d3a2f710d8f47d5d7a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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