Hydrochloric Acid → N6-(3-iodobenzyl)-2-Chloro-5'-O-ethyladenosine

HRID 6672

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.[I:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][NH2:34].Cl>>[I:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][NH:34][C:4]1[C:5]2[N:6]=[CH:7][N:8]([C:9]=2[N:10]=[C:2]([Cl:1])[N:3]=1)[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([OH:18])[C@H:12]1[OH:13]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 970123-Iodobenzylamine

HCID 110700822,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-beta-D-ribofuranosyl)-purine

Product 1

HCID 11038875N6-(3-iodobenzyl)-2-Chloro-5'-O-ethyladenosine

Procedure

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (63, 375 mg, 0.87 mmol) and 3-iodobenzylamine.HCl (1.31 mmol, 352 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 366 mg (0.67 mmol, 77%), mp 80–82° C.; Rf 0.53 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.97 (bs, 1H, NH), 8.40 (s, 1H, H-8), 7.74 (s, 1H, CCHCI), 7.60 (d, 1H, J=6.87 Hz, CCHCHCH), 7.35 (d, 1H, J=8.24 Hz, CCHCH), 7.12 (t, 1H, J=7.21 Hz, CCHCH), 5.84 (d, 1H, =4.46 Hz, H-1′), 5.56 (d, 1H, J=5.49 Hz, OH-2′), 5.30 (d, 1H, J=5.15 Hz, OH-3′), 4.60 (d, 2H, J=4.46 Hz, NHCH2), 4.51 (d, 1H, J=5.15 Hz, H-2′), 4.14–4.11 (m, 1H, H-3′), 4.02 (q, 1H, J=3.43 Hz, H-4′), 3.63–3.58 (m, 2H, H-5′), 3.49 (q, 2H, J=6.52 Hz, CH2CH3), 1.13 (t, 3H, J=6.52 Hz, CH3); MS m/z 546 (+H)+; Anal. (C19H21ClIN5O4.0.8 HCON(CH3)2) C, H, N.

Workup

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

Sources & evidence

ORD record: ord-2e0bdacdc5f54682a3efd2afc10f8706
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084127B2

Linked notes

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