Triethylamine → N-cyclopentoxy-2-methyladenosine

HRID 1647190Notes

Reaction equation

Cl.[CH:2]1([O:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C([O:12][C@@H:13]1[C@H:17]([O:18]C(=O)C)[C@@H:16]([CH2:22][O:23]C(=O)C)[O:15][C@H:14]1[N:27]1[CH:35]=[N:34][C:33]2[C:28]1=[N:29][C:30]([CH3:37])=[N:31][C:32]=2Cl)(=O)C.C(N(CC)CC)C>O1CCOCC1>[CH:2]1([O:7][NH:8][C:32]2[C:33]3[N:34]=[CH:35][N:27]([C:28]=3[N:29]=[C:30]([CH3:37])[N:31]=2)[C@@H:14]2[O:15][C@H:16]([CH2:22][OH:23])[C@@H:17]([OH:18])[C@H:13]2[OH:12])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

O-Cyclopentylhydroxylamine hydrochloride (0.52 g, 3.75 mmol) was reacted with 9-(2,3,5-triO-acetyl-β-D-ribofuranosyl)-6-chloro-2-methyl-9H-purine (1.07 g, 2.5 mmol) [prepared from 2-methylinosine (Journal of Organic Chemistry, 1967, 32, 3258-3260) by standard acylation and chlorination steps] in dioxan (40 ml) in the presence of triethylamine (0.63 g, 6.25 mmol). The reaction mixture was heated at 100° C. for 70 h, before being filtered and evaporated. The product (after purification by chromatography), followed by debenzoylation using methanolic ammonia to provide the title N-cyclopentoxy-2-methyladenosine (after column chromatography) as a foam 1H NMR (DMSO-d6)γ 1.47-1.93 (8H, m,--CH2CH2CH2CH2 --), 2.32 (3H, s,--CH3), 4.59 (1H, br m,--O--CH--), 5.88 (1H, d, H-1').

Workup

filtrationbefore being filtered
customevaporated
customThe product (after purification by chromatography)

Sources & evidence

ORD record: ord-23d04681bfb8485897b084116e386ee7
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430027

Reaction notes

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