1-Hexyne → HCID 69538223, compound

HRID 2216263Notes

Reaction equation

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

Participants

Reactant 2

HCID 127321-Hexyne

HCID 86592812HCID 86592812, compound

Product 1

HCID 69538223HCID 69538223, compound

Procedure

The reaction was performed with 2-iodo-8-methylaminoadenosine (7, 50 mg, 0.12 mmol) and 1-hexyn (0.58 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 36 mg (0.09 mmol, 79%), mp 161–163÷C; Rƒ 0.23 (5% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 7.01 (d, 1H, J=4.81 Hz, NH), 6.61 (s, 2H, NH2), 5.84 (d, 1H, J=7.55 Hz, H-1′), 5.78 (t, 1H, J=4.47 Hz, OH-2′), 5.26 (d, 1H, J=6.87 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.58 (q, 1H, J=5.83 Hz, H-2′), 4.10–4.03 (m, 1H, H-3′), 3.95 (bs, 1H, H-4′), 3.62 (bs, 2H, H-5′), 2.87 (s, 3H, J=4.46 Hz, NHCH3), 2.36 (t, 2H, J=6.87 Hz, ≡CCH2), 1.53–1.39 (m, 4H, CH2CH2), 0.89 (t, 3H, J=6.87 Hz, CH3); MS m/z 376 (M+H)+; Anal. (C17H24N6O4) C, H, N.

Workup

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

Sources & evidence

ORD record: ord-d6c9083590494f849aae6d8c80f81270
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112574B2

Reaction notes

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