HCID 86623416, compound → HCID 86623417, compound

HRID 2111354Notes

Reaction equation

HRID 2111354 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][N:9]([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([Cl:19])[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][N:9]([C:10]1[C:15]([NH2:16])=[CH:14][N:13]=[C:12]([Cl:19])[N:11]=1)[CH2:20][CH2:21][CH2:22][CH3:23])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 86623416HCID 86623416, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86623417HCID 86623417, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.6 g (0.0045 mole) of 3-[butyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propionic acid tert-butyl ester (IV-44) in 50 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 1.3 g of 3-[(5-amino-2-chloro-pyrimidin-4-yl)-butyl-amino]-propanoic acid tert-butyl ester (V-44). 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-cb872f35d1f4464aaee8f01a3cb5ca37
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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