HCID 87555184, compound → HCID 87618831, compound

HRID 2111364Notes

Reaction equation

HRID 2111364 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH3:22])[CH:6]([N:8]([C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:9]1[CH2:11][CH2:10]1)[CH3:7])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH3:22])[CH:6]([N:8]([C:12]1[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:9]1[CH2:11][CH2:10]1)[CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 87555184HCID 87555184, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 87618831HCID 87618831, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.02 g (0.003 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopropyl-amino]-2-methyl-butanoic acid ethyl ester (IV-46) 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 0.68 g of (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopropyl-amino]-2-methyl-butanoic acid ethyl ester (V-46). 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-0984b75980e148b095c33da3f7a12d32
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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