Dimethylamine → 1-(6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-chloropyrimidin-4-yl)-N,N-dimethylmethanamine

HRID 75458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75458
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][O:11][CH2:12]3)[CH:5]=[C:4]([CH2:16]Cl)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][NH:25][CH3:26]>CN(C=O)C>[CH:13]12[N:8]([C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([CH2:16][N:25]([CH3:26])[CH3:24])[CH:5]=3)[CH:9]([CH2:15][CH2:14]1)[CH2:10][O:11][CH2:12]2

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 866659078-(2-Chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane

Produkt 1

HCID 866659081-(6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-chloropyrimidin-4-yl)-N,N-dimethylmethanamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A flask was charged with 8-(2-chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (2.30 g, 8.39 mmol) and DMF (40 ml) was added to give a yellow solution. Potassium carbonate (2.90 g, 20.97 mmol) and dimethylamine (2.0M in THF, 4.6 ml, 9.23 mmol) were added and the reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was filtered through a Buchner funnel and washed with methylene chloride and ethyl acetate. The filtrate was concentrated to provide crude product as a brown oil, which solidified upon standing (2.61 g). The crude product was added to a silica gel column and was eluted with 0-10% methanol in methylene chloride to provide 1-(6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-chloropyrimidin-4-yl)-N,N-dimethylmethanamine (2.01 g, 85%) as an off-white solid. HRMS; [M+H]+ Obs'd=283.1320, [M+H]+ Calc'd=283.1319.

Aufarbeitung

  1. additionwas added
  2. customto give a yellow solution
  3. filtrationThe reaction mixture was filtered through a Buchner funnel
  4. washwashed with methylene chloride and ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customto provide crude product as a brown oil, which
  7. washwas eluted with 0-10% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-f2bcaf69764f424fbca75e5e95a553cc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835429B2

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