HCID 178477759, compound → HCID 178511303, compound

HRID 641154Notes

Reaction equation

HRID 641154 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[N:5]([CH2:8][C@@H:9]1[C@H:13]([OH:14])[C@H:12]([OH:15])[C@H:11]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[O:10]1)=[N+]=[N-]>C(O)C.[Pd]>[CH2-:1][C:2]([CH3:4])=[O:3].[NH2:5][CH2:8][C@@H:9]1[C@H:13]([OH:14])[C@H:12]([OH:15])[C@H:11]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[O:10]1

Participants

4

Reactant 1

HCID 178477759HCID 178477759, compound

Product 1

HCID 178511303HCID 178511303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (100 mg) was added to a solution of (4S,2R,3R,5R)-2-azidomethyl-5-[6-(tetrahydrofuran-3-yl)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide, a compound of formula (10) (314 mg), in ethanol (20 mL) and stirred under an atmosphere of hydrogen at room temperature for 16 hours. The catalyst was removed by filtration, and the solvent evaporated from the filtrate to give (4S,2R,3R,5R)-2-aminomethyl-5-[6-(tetrahydrofuran-3-yl)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide, a compound of formula (11).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated from the filtrate

Sources & evidence

ORD record
ord-7dcdb21f5082449fb0d4dcbc6a4f6e01
Source dataset
uspto-grants-2010_04
Patent number
US07696181B2

Reaction notes

Loading…