Sodium Azide → 7-(1-azidoethyl)-6-bromo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1429815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429815
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][S:11][C:5]2=[N:4][C:3]=1[CH:12](Br)[CH3:13].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:15]([CH:12]([C:3]1[N:4]=[C:5]2[S:11][CH:10]=[CH:9][N:6]2[C:7](=[O:8])[C:2]=1[Br:1])[CH3:13])=[N+:16]=[N-:17]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 581114456-bromo-7-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Produkt 1

HCID 866500717-(1-azidoethyl)-6-bromo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-7-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (3.7 g, 11 mmol) and sodium azide (1.4 g, 22 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 1.5 hour. After diluted with ethyl acetate, the mixture was washed with water, dried over Na2SO4, concentrated and purified on silica gel (0-60% ethyl acetate/hexanes) to give the desired product (2.16 g). LCMS calculated for C8H7BrN5OS (M+H)+: m/z=300.0. Found: 300.0.

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel (0-60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bf710446df6f474b8601c01dad6c6399
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940752B2

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