Ammonia → 2-Chloro-N-(2-phenoxyethyl)adenosine

HRID 1379631Notes

Reaction equation

HRID 1379631 reaction equation
Cl.[O:2]([CH2:9][CH2:10][NH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:20][C@@H:21]1[C@H:25]([O:26]C(=O)C2C=CC=CC=2)[C@@H:24]([CH2:35][O:36]C(=O)C2C=CC=CC=2)[O:23][C@H:22]1[N:45]1[CH:53]=[N:52][C:51]2[C:46]1=[N:47][C:48]([Cl:55])=[N:49][C:50]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C.N>O1CCOCC1>[Cl:55][C:48]1[N:49]=[C:50]([NH:11][CH2:10][CH2:9][O:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:51]2[N:52]=[CH:53][N:45]([C:46]=2[N:47]=1)[C@@H:22]1[O:23][C@H:24]([CH2:35][OH:36])[C@@H:25]([OH:26])[C@H:21]1[OH:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 458500(2-Aminoethoxy)benzene hydrochlorideHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 544488042-Chloro-N-(2-phenoxyethyl)adenosine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by reacting 2-phenoxyethylamine hydrochloride (0.80 g, 4.6 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol) in dioxan (25 ml) in the presence of triethylamine (1.0 g, 9.6 mmol) followed by deprotection of the purified product using methanolic ammonia to provide the title nucleoside (0.75 g, 60%)(following flash chromatography) as an amorphous foam, 1H NMR (DMSO-d6)δ 3.52-3.59 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.82 (2H, q, --OH2 --), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.52 (1H, q, H-2'), 5.12 (1H, t, 5'-0H), 5.25, 5.54 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.92-7.02 (3H, m, Ar--H), 7.26-7.34 (2H, t, Ar--H), 8.46 (1H, m, H-8), 8.56 (1H, br, t, N--H).

Sources & evidence

ORD record
ord-47811d1a5cf347a3b10ef650c1646814
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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