N-bromobutanimide → Methyl 6-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

HRID 1926872

Reaktionsgleichung

Reaktionsgleichung von HRID 1926872
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[Br:26]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([Br:26])=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 25123737Methyl 6-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

Produkt 1

HCID 25123738Methyl 6-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Put 1.75 g (5.15 mmol) 6-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoic acid methyl ester in 5.2 ml tetrachloromethane. At RT, add 1.054 g (5.92 mmol) N-bromosuccinimide and then heat the mixture under reflux for approx. 1 h. After cooling, concentrate by vacuum evaporation and chromatograph the residue on silica gel (solvent: cyclohexane/ethyl acetate 4:1). 0.89 g (41.2% of theor.) of the target compound is obtained.

Aufarbeitung

  1. temperatureheat the mixture
  2. temperatureunder reflux for approx. 1 h
  3. temperatureAfter cooling
  4. concentrationconcentrate by vacuum evaporation and chromatograph the residue on silica gel (solvent: cyclohexane/ethyl acetate 4:1)
  5. custom0.89 g (41.2% of theor.) of the target compound is obtained

Quellen und Nachweise

ORD-Eintrag
ord-b7872bcab40a47ccb02e4d4e23e68edd
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183246B2

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