Triethylamine → HCID 22877229, compound

HRID 1379641Notes

Reaction equation

HRID 1379641 reaction equation
[O:1]([C@H:8]([CH3:11])[CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:20][C@@H:21]1[C@H:25]([O:26]C(=O)C2C=CC=CC=2)[C@@H:24]([CH2:35][O:36]C(=O)C2C=CC=CC=2)[O:23][C@H:22]1[N:45]1[CH:53]=[N:52][C:51]2[C:46]1=[N:47][C:48]([Cl:55])=[N:49][C:50]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[Cl:55][C:48]1[N:49]=[C:50]([NH:10][CH2:9][C@H:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:11])[C:51]2[N:52]=[CH:53][N:45]([C:46]=2[N:47]=1)[C@@H:22]1[O:23][C@H:24]([CH2:35][OH:36])[C@@H:25]([OH:26])[C@H:21]1[OH:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 40429613HCID 40429613, compound

Product 1

HCID 22877229HCID 22877229, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-2-Phenoxy-1-propylamine (0.6 g, 2.9 mmol)(prepared by the method described in example 2) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.5 g, 2.4 mmol) in dioxan (20 ml) in the presence of triethylamine (0.5 g, 5.3 mmol). The reaction mixture was stirred at room temperature for 72 h before being filtered and evaporated. The product, following purification by flash chromatography, was treated with saturated methanolic ammonia (30 ml) for 18 h and evaporated to provide a solid residue. This solid was washed thoroughly with dichloromethane to provide the title 2-chloro- N-[(R)-2-phenoxy-1-propyl]adenosine (0.7 g, 65%), mp 175°-177° C., 1H NMR (DMSO-d6)δ 1.39 (3H, d, --CH3), 3.56 (1H, ABX, H-5'a), 3.68 (1H, m, H-5'b), 3.33-3.40 (1H, m, --C--H), 3.83-3.92 (1H, --C--H), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.53 (1H, dd, H-2'), 4.70 (1H, q, --C--H), 5.08, 5.34, 5.50 (3H, 3 br, 2', 3' and 5'-OH), 5.85 (1H, d, H-1'), 6.90 (1H, t, Ar--H), 7.11 (2H, d, Ar--H), 7.28 (2H, t, Ar--H), 8.45 (1H, s, H-8), 8.63 (1H, t, N--H).

Workup

  1. filtrationbefore being filtered
  2. customevaporated
  3. custompurification by flash chromatography
  4. additionwas treated with saturated methanolic ammonia (30 ml) for 18 h
  5. customevaporated
  6. customto provide a solid residue
  7. washThis solid was washed thoroughly with dichloromethane

Sources & evidence

ORD record
ord-0e95b83db15a484387a557c0b180e61a
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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