Ammonia → HCID 44322964, compound

HRID 1901524Notes

Reaction equation

HRID 1901524 reaction equation
[NH2:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]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.N>>[Cl:57][C:50]1[N:51]=[C:52]([NH:1][N:2]2[CH2:3][CH:4]=[C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][CH2:7]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

4

Reactant 3

HCID 222AmmoniaHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 135346934-Phenyl-3,6-dihydropyridin-1(2H)-amine

Product 1

HCID 44322964HCID 44322964, compoundYield 12%

Procedure

The title compound was prepared according to method A as described above by reacting crude 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine (prepared by the procedure outlined in Example 6) (1.25 g) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.50 g, 3.9 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-Chloro-N-(4-phenyl-1,2,3,6-tetrahydro-1-pyridinyl)adenosine (0.20 g 12%) (after column chromatography) as a foam, 1H NMR (DMSO-d6) δ 3.53-3.70 (4H, m, H-5'a, H-5'b and --CH2 --), 3.94 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.07 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.15 (1H, br s, vinylic C--H), 7.24-7.51 (5H, m, Ar--H), 8.43 (1H, s, H-8), 9.55 (1H, s, N--H).

Workup

  1. customThe title compound was prepared
  2. customprepared by the procedure

Sources & evidence

ORD record
ord-f6a3c25554e34232b3fb89f5e1e5d8ab
Source dataset
uspto-grants-1996_11
Patent number
US05578582

Reaction notes

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