Ammonia → 2-chloro-N-[2-(phenylmethoxy)ethyl]adenosine

HRID 1379642Notes

Reaction equation

HRID 1379642 reaction equation
Cl.[C:2]1([CH2:8][O:9][CH2:10][CH2:11][NH2:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:21][C@@H:22]1[C@H:26]([O:27]C(=O)C2C=CC=CC=2)[C@@H:25]([CH2:36][O:37]C(=O)C2C=CC=CC=2)[O:24][C@H:23]1[N:46]1[CH:54]=[N:53][C:52]2[C:47]1=[N:48][C:49]([Cl:56])=[N:50][C:51]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:56][C:49]1[N:50]=[C:51]([NH:12][CH2:11][CH2:10][O:9][CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:52]2[N:53]=[CH:54][N:46]([C:47]=2[N:48]=1)[C@@H:23]1[O:24][C@H:25]([CH2:36][OH:37])[C@@H:26]([OH:27])[C@H:22]1[OH:21]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27947862-(Benzyloxy)ethanamine hydrochlorideHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 538942872-chloro-N-[2-(phenylmethoxy)ethyl]adenosineYield 44%

Procedure

The title compound was prepared by reacting 2-(phenylmethoxy)ethylamine hydrochloride (0.51 g, 2.7 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.43 g, 2.25 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro- N-[2-(phenylmethoxy)ethyl]adenosine (0.38 g, 44%)(after column chromatography) as a solid, mp 115°-124° C., 1H NMR (DMSO-d6)δ 3.50-3.58 (1H, m, H-5'a), 3.60-3.70 (4H, m, H-5'b, --CH2 -- and --CH--), 3.95 (1H, q, H-4'), 4.04-4.16 (2H, m, H-3' and --CH--), 4.52 (1H, br s, H-2' and --CH2 --), 5.07 (1H, t, 5'-0H), 5.21, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.22-7.36 (5H, m, Ar--H), 8.25-8.40 (2H, m, H-8 and N--H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f01948b2b557422fab55cc704ed38416
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

Loading…