Methyl 3-azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate → Methyl 3-amino-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate

HRID 1289373Notes

Reaction equation

HRID 1289373 reaction equation
[N:1]([C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH:5]([O:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH:5]([O:10][C:11]1[N:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[N:16]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 15789719Methyl 3-azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate

Product 1

HCID 18921361Methyl 3-amino-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3.7 g (10 mmol) of methyl 3-azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate (Ex. 2) are dissolved in 20 ml of methanol/ethyl acetate (1:1), treated with 400 mg of Pd/C 10% and stirred for 6 h under a hydrogen atmosphere. After filtering off the catalyst and concentrating, a colorless oil is obtained which solidifies after a few days.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationconcentrating
  3. customa colorless oil is obtained which
  4. waitsolidifies after a few days

Sources & evidence

ORD record
ord-48350b01220f4a41953ea6e55c352be0
Source dataset
uspto-grants-1998_05
Patent number
US05750469

Reaction notes

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