Ethyl Acetate → 5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methyl-N-(pyrrolidin-1-yl)pyrimidin-4-amine

HRID 641683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641683
[Br:1][C:2]1[C:3]([NH:16][NH2:17])=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8].[CH3:18][C:19](N(C)C)=O.[CH3:24][CH2:25]OC(C)=O>>[Br:1][C:2]1[C:3]([NH:16][N:17]2[CH2:18][CH2:19][CH2:25][CH2:24]2)=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8]

Komponenten

4

Edukt 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 592589011-(5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)hydrazine

Produkt 1

HCID 592589815-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methyl-N-(pyrrolidin-1-yl)pyrimidin-4-amine

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a flask was added 1-(5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)hydrazine (100 mg, 0.34 mmol) 1,4-dibromobutane (0.04 ml, 0.37 mmol) hunig's base (0.18 ml, 1.01 mmol) and DMAC (1.0 ml) at R.T. After heating at 60° C. over night, the reaction mixture was cooled to R.T. and diluted with EtOAc (2 ml) the white solid was filtered and the mother liquor was concentrated under reduced pressure. The resulting residue was purified by column chromatography eluted with 30% EtOAc:hex to give the titled compound weighted 76 mg 64%

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to R.T.
  2. filtrationwas filtered
  3. concentrationthe mother liquor was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography
  5. washeluted with 30% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-07381ae7b8e64c82b3eb2c104e3f2d70
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696213B2

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