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 2111329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111329
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-046545665fd04542a3514dc343ecc2c1
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517873B2

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