[(R)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester → [(R)-1-(5-amino-2-chloro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester

HRID 2111441Notes

Reaction equation

HRID 2111441 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([Cl:19])[N:11]=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[C:15]([NH2:16])=[CH:14][N:13]=[C:12]([Cl:19])[N:11]=1

Participants

5

Reactant 2

HCID 86623422[(R)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86623423[(R)-1-(5-amino-2-chloro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.3 g (0.011 mole) of [(R)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester (IV-102) in 150 mL of ethyl acetate and 0.8 g of 10% 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. The filtrate was concentrated under reduced pressure to give [(R)-1-(5-amino-2-chloro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester (V-102), which also contained a small amount of (R)-9-chloro-2,3,3a,4-tetrahydro-1H,6H-6,8,10,10b-tetraaza-benzo[e]azulen-5-one. 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. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1ed630dd1624f4ba84067650df1bbbf
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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