Cyclopentylamine → N6-Cyclopentyl-2-chloro-5'-O-methyladenosine

HRID 6667

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][CH3:26])[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([NH:33][C:4]2[C:5]3[N:6]=[CH:7][N:8]([C:9]=3[N:10]=[C:2]([Cl:1])[N:3]=2)[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([OH:18])[C@H:12]2[OH:13])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 110698082,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purine

Product 1

HCID 10045523N6-Cyclopentyl-2-chloro-5'-O-methyladenosine

Procedure

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (61, 505 mg, 1.2 mmol) and cyclopentylamine (1.8 mmol, 178 μL). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 364 mg (0.95 mmol, 79%), mp 124–126° C.; Rf 0.15 (eluens 2% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.33 (bs, 1H, NH), 8.30 (s, 1H, H-8), 5.81 (d, 1H, J=4.46 Hz, H-1′), 5.51 (d, 1H, J=3.36 Hz, OH-2′), 5.29 (d, 1H, J=3.32 Hz, OH-3′), 4.59–4.29 (m, 2H, CH, H-2′), 4.41–3.99 (m, 2H, H-3′,4′), 3.56–3.52 (m, 2H, H-5′), 1.94–1.92 (m, 2H, cyclopentyl), 1.71–1.50 (m, 4H, cyclopentyl); MS m/z 384 (M+H)+; Anal. (C16H22ClN5O4.0.1 CH2Cl2) C, H, N.

Workup

customThe mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-fc7530688a2b4b59b6358241b17eba03
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084127B2

Linked notes

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