Diisopropylethylamine → (5-Bromo-pyrimidin-2-yl)-(2-fluoro-5-trifluoromethyl-benzyl)-amine

HRID 604017

Reaktionsgleichung

Reaktionsgleichung von HRID 604017
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][NH2:5].C(N(CC)C(C)C)(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1>O1CCOCC1>[Br:23][C:24]1[CH:25]=[N:26][C:27]([NH:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:2]=2[F:1])=[N:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5338392-Fluoro-5-(trifluoromethyl)benzylamineHCID 6066655-Bromo-2-chloropyrimidine

Produkt 1

HCID 67087263(5-Bromo-pyrimidin-2-yl)-(2-fluoro-5-trifluoromethyl-benzyl)-amineAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Fluoro-5-trifluoromethyl-benzylamine (2.0 g) is dissolved in 1,4-dioxane (10 ml) and thereto are added N,N-diisopropylethylamine (2.7 ml) and 5-bromo-2-chloropyrimidine (3.02 g) and the mixture is heated under reflux overnight. The reaction solution is cooled to room temperature and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give (5-bromo-pyrimidin-2-yl)-(2-fluoro-5-trifluoromethyl-benzyl)-amine (1.69 g). MS (m/z): 350/352 [M+H]+

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-c9fa896eb09347a6a53ef3edf4b3a726
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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