Ammonia → HCID 54487654, compound

HRID 1901530Notes

Reaction equation

HRID 1901530 reaction equation
OCC1CCCCN1.[NH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O:32][C@@H:33]1[C@H:37]([O:38]C(=O)C2C=CC=CC=2)[C@@H:36]([CH2:47][O:48]C(=O)C2C=CC=CC=2)[O:35][C@H:34]1[N:57]1[CH:65]=[N:64][C:63]2[C:58]1=[N:59][C:60]([Cl:67])=[N:61][C:62]=2Cl)(=O)C1C=CC=CC=1.N>>[C:18]1([S:17][CH2:16][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][NH:10]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1.[Cl:67][C:60]1[N:61]=[C:62]([NH:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH2:16][S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:63]2[N:64]=[CH:65][N:57]([C:58]=2[N:59]=1)[C@@H:34]1[O:35][C@H:36]([CH2:47][OH:48])[C@@H:37]([OH:38])[C@H:33]1[OH:32]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 94263Piperidin-2-ylmethanolHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 23367729HCID 23367729, compound

Product 2

HCID 23367716HCID 23367716, compoundHCID 54487654HCID 54487654, compoundYield 10.3%

Procedure

2-(Phenylthiomethyl)piperidine was prepared from 2-(hydroxymethyl)piperidine by the method described by Kotsuki et al., Tetrahedron Letters, 1991, 32, 4155-4158; otherwise the synthesis proceeded as described in Example 16. 1-Amino-2-(phenylthiomethyl)piperidine (1.4 g, 6.5 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.25 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-[2-(phenylthiomethyl)-1-piperidinyl]adenosine (0.17 g, 10%) as a foam (a mixture of diastereoisomers); 1H NMR (DMSO-d6) δ 3.51-3.59 (1H, m, H-5'a), 3.62-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.47-4.56 (1H, m, H-2'), 5.06 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.82-5.87 (1H, 2d, H-1'), 7.16-7.54 (5H, 2m, Ar--H), 8.41, 8.46 (1H, 2s, H-8), 9.40 (1H, s, N--H).

Sources & evidence

ORD record
ord-f99c6ec9b2b447a990de30c59788495b
Source dataset
uspto-grants-1996_11
Patent number
US05578582

Reaction notes

Loading…