Cesium carbonate → 6-Chloro-2-[2-(4-chlorophenyl)-ethoxy]-9-(2,3,5-tri-o-acetyl-beta-d-ribofuranosyl)purine

HRID 966387Notes

Reaction equation

HRID 966387 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([OH:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]1[O:14][C:15](=[O:17])[CH3:16].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38]Br)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]([O:11][CH2:38][CH2:37][C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]1[O:14][C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 1784763556-Chloro-2-hydroxy-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine

Product 1

HCID 591072566-Chloro-2-[2-(4-chlorophenyl)-ethoxy]-9-(2,3,5-tri-o-acetyl-beta-d-ribofuranosyl)purineYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 2, Step C) and 2-(4-chlorophenyl)ethyl bromide (300.1 g, 1.36 mol) in dimethylformamide (7,280 mL), cesium carbonate (665 g, 2.04 mol) was added. The reaction was allowed to stir under inert atmosphere for 32 hours. The reaction was concentrated under reduced pressure and partitioned between dichloromethane and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography eluting with ethyl acetate/heptanes to yield a yellow solid of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine Typical Yield: 64%

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompartitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography
  8. washeluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-120c3525dea745b5be28d817e329140e
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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