HCID 69467950, compound → HCID 69467061, compound

HRID 1793797Notes

Reaction equation

HRID 1793797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C@H:10]2[O:14][C@@H:13]([N:15]3[CH:23]=[N:22][C:21]4[C:16]3=[N:17][CH:18]=[N:19][C:20]=4[NH:24][CH:25]3[CH2:29][CH2:28][O:27][CH2:26]3)[C@H:12]([OH:30])[C@@H:11]2[OH:31])=[CH:4][CH:3]=1>C(O)C.C1CCCCC=1.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]2[O:14][C@@H:13]([N:15]3[CH:23]=[N:22][C:21]4[C:16]3=[N:17][CH:18]=[N:19][C:20]=4[NH:24][CH:25]3[CH2:29][CH2:28][O:27][CH2:26]3)[C@H:12]([OH:30])[C@@H:11]2[OH:31])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 69467950HCID 69467950, compound

Product 1

HCID 69467061HCID 69467061, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

To a solution of 5-[2-(4-fluorophenyl)vinyl](4S,2R,3R,5R)-2-[6-(oxolan-3-ylamino)purin-9-yl]oxolane-3,4-diol (40 mg) in ethanol (5 ml) and cyclohexene (2 ml) was added palladium hydroxide (50 mg), and the mixture was stirred for 24 hours. The catalyst was filtered off, and solvent removed under reduced pressure. The residue was purified by preparative thin layer chromatography, to give pure (4S,2R,3R,5R)-5-[2-(4-fluorophenyl)ethyl]-2-[6-(oxolan-3-ylamino)purin-9-yl]oxolane-3,4-diol, a compound of Formula I.

Workup

  1. filtrationThe catalyst was filtered off
  2. customsolvent removed under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-80103e80c64444f89518837dd029ac88
Source dataset
uspto-grants-2006_04
Patent number
US07022681B2

Reaction notes

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