3-[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester → 3-[(5-Amino-2-chloro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester

HRID 2111348Notes

Reaction equation

HRID 2111348 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]([C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]([Cl:22])[N:14]=1)[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]([C:13]1[C:18]([NH2:19])=[CH:17][N:16]=[C:15]([Cl:22])[N:14]=1)[CH:10]([CH3:12])[CH3:11])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 866234133-[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 866234143-[(5-Amino-2-chloro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl esterYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.6 g (0.0045 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester (IV-43) 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 1.4 g of 3-[(5-amino-2-chloro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester (V-43). 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-e21fa1e244bc44df82d10be391e79752
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

Loading…