9-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine → HCID 44323567, compound

HRID 1901518Notes

Reaction equation

HRID 1901518 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O:22][C@@H:23]1[C@H:27]([O:28]C(=O)C2C=CC=CC=2)[C@@H:26]([CH2:37][O:38]C(=O)C2C=CC=CC=2)[O:25][C@H:24]1[N:47]1[CH:55]=[N:54][C:53]2[C:48]1=[N:49][C:50]([Cl:57])=[N:51][C:52]=2Cl)(=O)C1C=CC=CC=1>>[Cl:57][C:50]1[N:51]=[C:52]([NH:1][N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:53]2[N:54]=[CH:55][N:47]([C:48]=2[N:49]=1)[C@@H:24]1[O:25][C@H:26]([CH2:37][OH:38])[C@@H:27]([OH:28])[C@H:23]1[OH:22]

Participants

3

Reactant 2

HCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 18926399HCID 18926399, compound

Product 1

HCID 44323567HCID 44323567, compound

Procedure

The title compound was prepared according to method A as described in Example 1 was obtained as a solid (0.25 g, 26%) by the reaction of 1-amino-2-phenylpiperidine (Overberger, C. G. and Herin, L. P. Journal of Organic Chemistry, 1962, 27, 417) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine, followed by deprotection (as described in Example 5) to give the title nucleoside (a ca. 60:40 mixture of diastereoisomers): m.p. 186°-210° C.; 1H NMR (400 MHz, Me2SO-d6) δ 3.47-3.20 (2H, m, 5'-CH2), 3.82-3.97, 4.04-4.14 (2H, 2m, H-3' and H-4'), 4.46-4.56 (1H, 2q, H-2'), 5.33, 5.73 (1H, 2d, H-1'), 8.26, 8.48 (1H, 28, H-8).

Sources & evidence

ORD record
ord-1ab12dbd045a423598b94752d981f461
Source dataset
uspto-grants-1996_11
Patent number
US05578582

Reaction notes

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