3-[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester → 3-[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester

HRID 2111329Notes

Reaction equation

HRID 2111329 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([CH3:23])([CH3:22])[CH2:5][N:6]([C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:24])[C:4]([CH3:22])([CH3:23])[CH2:5][N:6]([C:12]1[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 866234093-[(2-Chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester

Product 1

HCID 866234103-[(5-Amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl esterYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 27.32 g (0.0767 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester (IV-38), 8.21 g of 5% palladium on carbon catalyst and 700 mL of ethyl acetate was stirred under an atmosphere of hydrogen until the reaction was complete. The resulting mixture was filtered through Celite, washing the filter pad with ethyl acetate, and the filtrate was concentrated under reduced pressure to give 25.33 g of 3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoic acid methyl ester (V-38) as a light brown oil.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. washwashing the filter pad with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-046545665fd04542a3514dc343ecc2c1
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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