Ammonia → HCID 44323083, compound

HRID 1647526Notes

Reaction equation

HRID 1647526 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C([O:23][C@@H:24]1[C@H:28]([O:29]C(=O)C2C=CC=CC=2)[C@@H:27]([CH2:38][O:39]C(=O)C2C=CC=CC=2)[O:26][C@H:25]1[N:48]1[CH:56]=[N:55][C:54]2[C:49]1=[N:50][C:51]([Cl:58])=[N:52][C:53]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:58][C:51]1[N:52]=[C:53]([NH:1][N:2]2[CH2:7][CH2:6][CH:5]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:4][CH2:3]2)[C:54]2[N:55]=[CH:56][N:48]([C:49]=2[N:50]=1)[C@@H:25]1[O:26][C@H:27]([CH2:38][OH:39])[C@@H:28]([OH:29])[C@H:24]1[OH:23]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10679905HCID 10679905, compoundHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 44323083HCID 44323083, compoundYield 65%

Procedure

1-Amino-4-phenylthiopiperidine (1.10 g, 6.7 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.5 g, 4 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(4-phenylthio-1-piperidinyl)adenosine (1.25 g, 65%) as a foam, 1H NMR (DMSO-d6) δ3.51-3.60 (1H, m, H-5'a), 3.62-3.68 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.50 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.21, 5.50 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 7.24-7.45 (5H, 2m, Ar-H), 8.41 (1H, s, H-8), 9.44 (1H, s, N-H).

Sources & evidence

ORD record
ord-bf1cc85a9a484a039ce1083625bff5f4
Source dataset
uspto-grants-1995_07
Patent number
US05432164

Reaction notes

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