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

HRID 58268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58268
[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-f2b7c86a945d41dca73116df1a92a05c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434746B2

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