5-Bromo-2,4-dichloropyrimidine → Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine

HRID 82298

Reaktionsgleichung

Reaktionsgleichung von HRID 82298
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]12([NH2:15])[CH2:14][CH:12]([CH2:13]1)[CH2:11]2>C(#N)C>[C:10]12([NH:15][C:3]3[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=3)[CH2:14][CH:12]([CH2:13]1)[CH2:11]2

Komponenten

4

Edukt 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 11469065Bicyclo(1.1.1)pentan-1-amine

Produkt 1

HCID 86672128Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 5-Bromo-2,4-dichloro-pyrimidine (6 g, 26.3 mmol) and bicyclo[1.1.1]pent-1-ylamine (4.7 g, 39.5 mmol) in acetonitrile (60 mL), was added TEA (16.5 mL, 118 mmol), and the mixture was stirred at 25° C. for 18 hours. The volatiles were removed in vacuo and the residue partitioned between water and EtOAc. The organic phase was dried (Na2SO4) and evaporated in vacuo. Purification by column chromatography on silica gel (EtOAc:Hexane 1:99) afforded the title compound as a white solid in 82% yield, 4.8 g.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customPurification by column chromatography on silica gel (EtOAc:Hexane 1:99)

Quellen und Nachweise

ORD-Eintrag
ord-5986d92af0194edf8983e02e6df604c3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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