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Methanol → 2-Amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

HRID 1274781
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1274781
CO.[NH2:3][C:4]1[C:9]([F:10])=[C:8]([Br:11])[C:7](Cl)=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1>[Pd].C(N(CC)CC)C>[NH2:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1.[NH2:3][C:4]1[C:9]([F:10])=[C:8]([Br:11])[CH:7]=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 887MethanolHCID 221211602-Amino-4-bromo-5-chloro-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

Produkt 2

HCID 177787632-Amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridineHCID 221212652-Amino-4-bromo-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938Palladium
Katalysator
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 10 ml of methanol were added 1.6 g of 2-amino-4-bromo-5-chloro-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine together with 0.47 g of triethylamine and 0.09 g of 10% palladium on carbon, and the mixture was hydrogenated at room temperature for 39 hours. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. To the residue was added 50 ml of chloroform, and the mixture was washed with 50 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography (silica gel, 25 g; eluent: chloroform) to obtain 0.75 g of 2-amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine as a pale brown oil, and 0.2 g of 2-amino-4-bromo-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine as a brown oil.

Aufarbeitung

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent and the like were distilled off under reduced pressure
  3. additionTo the residue was added 50 ml of chloroform
  4. washthe mixture was washed with 50 ml of distilled water
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6f064547ad044d53837ae0f4176a71ce
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06156903

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