Ammonia → HCID 10042350, compound

HRID 1647184Notes

Reaction equation

[CH3:1][O:2][NH2:3].C([O:12][C@@H:13]1[C@H:17]([O:18]C(=O)C2C=CC=CC=2)[C@@H:16]([CH2:27][O:28]C(=O)C2C=CC=CC=2)[O:15][C@H:14]1[N:37]1[CH:45]=[N:44][C:43]2[C:38]1=[N:39][C:40]([Cl:47])=[N:41][C:42]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:47][C:40]1[N:41]=[C:42]([NH:3][O:2][CH3:1])[C:43]2[N:44]=[CH:45][N:37]([C:38]=2[N:39]=1)[C@@H:14]1[O:15][C@H:16]([CH2:27][OH:28])[C@@H:17]([OH:18])[C@H:13]1[OH:12]

Participants

Reactant 3

HCID 222Ammonia

HCID 4113O-Methylhydroxylamine

HCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 10042350HCID 10042350, compoundYield 60.3%

Procedure

The title compound was prepared according to method A as described in example 4 by reacting O-methylhydroxylamine (0.20 g, 2.0 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.27 g, 2.0 mmol) and debenzoylating the purified product using methanolic ammonia to provide the title 2-chloro-N-methoxyadenosine (0.40 g, 45%) (after column chromatography) as a colourless foam which became crystalline on trituration with dichloromethane, providing 0.20 g of a white solid, mp 123°-125° C. 1H NMR (DMSO-d6)γ 3.52-3.59 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.78 (3H, s,--OCH3), 3.96 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.06 (1H, t, 5'-OH), 5.22, 5.51 (2H, 2d, 2'- and 3'-OH), 5.87 (1H, d, H-1'), 8.50 (1H, s, H-8), 11.60 (1H, s, N-H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-8a84c86459474707a8c7d74304a8d236
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430027

Reaction notes

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