Ammonia → HCID 10047835, compound

HRID 1379646Notes

Reaction equation

HRID 1379646 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH2:10].C([O:19][C@@H:20]1[C@H:24]([O:25]C(=O)C2C=CC=CC=2)[C@@H:23]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:22][C@H:21]1[N:44]1[CH:52]=[N:51][C:50]2[C:45]1=[N:46][C:47]([Cl:54])=[N:48][C:49]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:54][C:47]1[N:48]=[C:49]([NH:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:50]2[N:51]=[CH:52][N:44]([C:45]=2[N:46]=1)[C@@H:21]1[O:22][C@H:23]([CH2:34][OH:35])[C@@H:24]([OH:25])[C@H:20]1[OH:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 812922-MethoxybenzylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 10047835HCID 10047835, compoundYield 45.9%

Procedure

The title compound was prepared by reacting (2-methoxyphenyl)methylamine (0.55 g, 4.0 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.01 g, 1.6 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro- N-[(2-methoxyphenyl)methyl]adenosine (0.31 g, 45%)(after column chromatography) as a solid, mp 116°-119° C., 1H NMR (DMSO-d6)δ 3.51-3.60 (1H, m, H-5'a), 3.61-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.13 (1H, m, H-3'), 4.52 (1H, q, H-2'), 5.06 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.83-7.25 (4H, 2t, 2d, Ar--H), 8.43 (1H, s, H-8), 8.72 (1H, t, N--H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-97accdb48331490389a8123e3c567df5
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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