HCID 87619349, compound → HCID 87618835, compound

HRID 2111393Notes

Reaction equation

HRID 2111393 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][N:7]([C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([Cl:23])[N:15]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH3:13])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][N:7]([C:14]1[C:19]([NH2:20])=[CH:18][N:17]=[C:16]([Cl:23])[N:15]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH3:13])[CH3:2]

Participants

5

Reactant 2

HCID 87619349HCID 87619349, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 87618835HCID 87618835, compoundYield 82.3%

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-methyl-cyclopentyl)-amino]-propanoic acid ethyl ester (IV-57) 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 of the filtrate under reduced pressure gave 2.5 g of (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-(2-methyl-cyclopentyl)-amino]-propanoic acid ethyl ester (V-57). 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

Sources & evidence

ORD record
ord-5812c8d503de4648a4138df6c0e61e41
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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