Triethylamine → HCID 22877225, compound

HRID 1379640Notes

Reaction equation

HRID 1379640 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.FC1C=CC(O)=CC=1.C([O:29][C@@H:30]1[C@H:34]([O:35]C(=O)C2C=CC=CC=2)[C@@H:33]([CH2:44][O:45]C(=O)C2C=CC=CC=2)[O:32][C@H:31]1[N:54]1[CH:62]=[N:61][C:60]2[C:55]1=[N:56][C:57]([Cl:64])=[N:58][C:59]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[Cl:64][C:57]1[N:58]=[C:59]([NH:10][C@H:8]([CH3:9])[CH2:7][O:6][C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=2)[C:60]2[N:61]=[CH:62][N:54]([C:55]=2[N:56]=1)[C@@H:31]1[O:32][C@H:33]([CH2:44][OH:45])[C@@H:34]([OH:35])[C@H:30]1[OH:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97324-FluorophenolHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 25803002HCID 25803002, compound

Product 1

HCID 22877225HCID 22877225, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-1-(4-fluorophenoxy)-2-propylamine (0.29 g, 1.4 mmol)(prepared from 4-fluorophenol by the method desrcribed in example 2) was reacted with 9-(2',3',5'-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.89 g, 1.4 mmol) in dioxan (30 ml) in the presence of triethylamine (0.42 g, 3 mmol). The reaction mixture was stirred at room temperature for 18 h, and heated at 60° C. for 4 h. The reaction mixture was filtered and evaporated to a residue which was purified by flash chromatography. The resultant 2',3',5'-tri- O-benzoyl-2-chloro- N-[(R)-1-(4-fluorophenoxy)-2-propyl]adenosine was deprotected using methanolic ammonia to provide the title 2-chloro- N-[(R)-1-(4-fluorophenoxy)-2-propyl]adenosine (0.21 g, 40%)(after column chromatography), mp 172°-173° C.; 1H NMR (DMSO-d6)δ 1.29 (3H, d, --CH3), 3.52-3.60 (1H, m, H-5'a), 3.64-3.72 (1H, m, H-5'b), 3.92-4.00 (2H, m, H-4' and --C--H), 4.05-4.20 (2H, m, H-3' and --C--H), 4.53 (1H, m, H-2'), 4.65 (1H, m, --CH3C H--), 5.08, 5.24, 5.50 (3H, 3 br, 2', 3' and 5'-OH), 5.86 (1H, d, H-1'), 6.89-7.15 (4H, 2 m, Ar--H), 8.30-8.46 (2H, m, H-8 and N--H).

Workup

  1. temperatureheated at 60° C. for 4 h
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to a residue which
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-7cf07368af8b428d8448d4ca099a39b8
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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