Ammonia → 2-Chloro-N-[(R)-1-phenyl-2-propyl]adenosine

HRID 1379632Notes

Reaction equation

HRID 1379632 reaction equation
[CH3:1][C@@H:2]([NH2:10])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.C([O:19][C@@H:20]1[C@H:24]([O:25]C(=O)C2C=CC=CC=2)[C@@H:23]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:22][C@H:21]1[N:44]1[CH:52]=[N:51][C:50]2[C:45]1=[N:46][C:47]([Cl:54])=[N:48][C:49]=2Cl)(=O)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.N>O1CCOCC1>[Cl:54][C:47]1[N:48]=[C:49]([NH:10][C@H:2]([CH3:1])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:50]2[N:51]=[CH:52][N:44]([C:45]=2[N:46]=1)[C@@H:21]1[O:22][C@H:23]([CH2:34][OH:35])[C@@H:24]([OH:25])[C@H:20]1[OH:19]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 32893(-)-AmphetamineHCID 81531DiisopropylethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 151017792-Chloro-N-[(R)-1-phenyl-2-propyl]adenosineYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by reacting L-amphetamine (0.49 g, 3.6 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.9 g, 3.0 mmol) in dioxan (25 ml) in the presence of diisopropylethylamine (0.58 g, 4.5 mmol) followed by deprotection of the purified product using methanolic ammonia. Evaporation of the reaction mixture provided a gummy residue which crystallized on addition of dichloromethane (10 ml), to provide the title compound (0.26 g, 38%) as a solid, m.p. 132.5°-135.5° C. A further sample of the title compound (0.26 g) was obtained by flash chromatography of the mother liquors. 1H NMR (DMSO-d6)δ 1.22 (3H, d, -- CH3), 2.67-2.79 & 2.92-3.03 (2H, 2m, -- CH2 --), 3.51-3.58 (1H, m, H-5'a), 3.62-3.68 (1H, m, H-5'b), 3.94 (1H, q, H-4'), 4.12 (1H, m, H-3'), 4.41-4.54 (2H, m, H-2' and CH3C H--), 5.06 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2' and 3'-OH), 5.82 (1H, d, H-1'), 7.10-7.33 (5H, m, Ar--H), 8.28-8.44 (2H, m, H-8 and N--H).

Workup

  1. customThe title compound was prepared
  2. customEvaporation of the reaction mixture
  3. customprovided a gummy residue which
  4. customcrystallized on addition of dichloromethane (10 ml)

Sources & evidence

ORD record
ord-2fe12e06a3b64d3086827afb8331306c
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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