Cyclopentylamine → N6-cyclopentyl-5'-O-methyladenosine

HRID 6665

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([NH:32][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=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])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 109490246-chloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purine

Product 1

HCID 10904208N6-cyclopentyl-5'-O-methyladenosine

Procedure

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 589 mg, 1.53 mmol) and cyclopentylamine (2.3 mmol, 227 μl). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 476 mg (1.36 mmol, 89%), mp 164–166° C.; Rf 0.51 (eluens 10% MeOH in CH2Cl2). The product was re-crystallized from CH3CN); 1H NMR (DMSO-d6) δ 8.28 (s, 1H, H-8), 8.18 (s, 1H, H-2), 7.70 (d, 1H, J=7.55 Hz, NH), 5.89 (d, 1H, J=4.80 Hz, H-1′), 5.50 (d, 1H, J=5.15 Hz, OH-2′), 5.26 (d, 1H, J=5.15 Hz, OH-3′), 4.56 (q, 1H, J=4.12 Hz, H-2′), 4.13 (q, 1H, J=4.46 Hz, H-3′), 3.99 (q, 1H, J=4.12 Hz, H-4′), 3.57–3.42 (m, 2H, H-5′), 3.28 (s, 3H, OCH 3), 2.01–1.83 (m, 2H, cyclopentyl), 1.73–1.52 (m, 4H, cyclopentyl); MS m/z 350 (M+H)+; Anal. (C16H23N5O4.0.7 CH3CN) C, H, N.

Workup

customThe mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)
customThe product was re-crystallized from CH3CN)

Sources & evidence

ORD record: ord-ecf7348b03414725beb44f80588a50aa
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084127B2

Linked notes

Loading…