HCID 87618333, compound → HCID 87619003, compound

HRID 2111405Notes

Reaction equation

HRID 2111405 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][N:7]([C:15]1[C:20]([N+:21]([O-])=O)=[CH:19][N:18]=[C:17]([Cl:24])[N:16]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH3:14])[CH3:13])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][N:7]([C:15]1[C:20]([NH2:21])=[CH:19][N:18]=[C:17]([Cl:24])[N:16]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH3:14])[CH3:13])[CH3:2]

Participants

5

Reactant 2

HCID 87618333HCID 87618333, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 87619003HCID 87619003, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.3 g (0.0093 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(2,2-dimethyl-cyclopentyl)-amino]-propionic acid ethyl ester (IV-59) in 30 mL of ethyl acetate and 0.5 g of 5% palladium on carbon catalyst was stirred under an atmosphere of hydrogen until hydrogen uptake was complete. The mixture was filtered through a pad of Celite, washing the filter pad with dichloromethane. Concentration under reduced pressure gave 2.5 g of (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-cyclopentyl)-amino]-propanoic acid ethyl ester (V-59). This material was used directly in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing the filter pad with dichloromethane
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1537abac47d3439098fc813ccea2b87f
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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