Methanol → 6-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N4-isopropylpyrimidine-4,5-diamine 3-(dimethylamino)propanoate

HRID 75442

Reaktionsgleichung

Reaktionsgleichung von HRID 75442
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([NH:16][CH:17]([CH3:19])[CH3:18])[C:10]=1[N+:20]([O-])=O)[CH2:2]2.[OH2:23].NN.[CH3:26][OH:27]>[Ni]>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([NH:16][CH:17]([CH3:18])[CH3:19])[C:10]=1[NH2:20])[CH2:2]2.[CH3:4][N:3]([CH3:9])[CH2:2][CH2:1][C:26]([O-:27])=[O:23]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 866658976-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropyl-5-nitropyrimidin-4-amine

Produkt 1

HCID 866658986-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N4-isopropylpyrimidine-4,5-diamine 3-(dimethylamino)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

6-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropyl-5-nitropyrimidin-4-amine (47, 1.45 g, 4.42 mmoles) was dissolved in methanol and Raney™ nickel (approx. 2:1 by weight with respect to starting material) was added under a nitrogen atmosphere. Hydrazine hydrate (0.833 mL, 26.54 mmoles) was added and the reaction mixture was stirred at room temperature for 18 hours, filtered over Celite™, and the filtrate was concentrated to provide 6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N4-isopropylpyrimidine-4,5-diamine 3-(dimethylamino)propanoate (48) as a tan solid. Yield: 1.25 g (95%). LCMS (HP walk-on); 3.45 min., 298.5, M+H.

Aufarbeitung

  1. filtrationfiltered over Celite™
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-97b8449b76b5493bb9dd1f4712c68099
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835429B2

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