Sodium Azide → 6-Azido-4-(quinolin-6-yloxy)-pyrimidine

HRID 2264566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264566
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:19]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1)=[N+:20]=[N-:21]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 576000846-(6-Chloropyrimidin-4-yloxy)quinoline

Produkt 1

HCID 862346386-Azido-4-(quinolin-6-yloxy)-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 9.4 g (36.4 mMol) of 6-chloro-4-(quinolin-6-yloxy)-pyrimidine in 110 ml DMF, 4.74 g (73 mMol) NaN3 are added. After stirring for 60 min at 60° C., the solution is diluted with EtOAc and water. The aqueous layer is separated off and extracted 2× with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrate in vacuo to give the crude title compound which is used as such in the next step: MS: [M+1]+=265.

Aufarbeitung

  1. customThe aqueous layer is separated off
  2. extractionextracted 2× with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09cd8d930764423eb407ad7bcf53dc3d
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855215B2

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