Dimethylformamide → 5-Bromopyrimidine-2-carbonyl chloride

HRID 1027699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1027699
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Br:7][C:8]1[CH:9]=[N:10]C(C(O)=O)=[N:12][CH:13]=1.CN(C)C=O>ClCCl.CN(C)C=O.CO>[Br:7][C:8]1[CH:13]=[N:12][C:1]([C:2]([Cl:4])=[O:3])=[N:10][CH:9]=1

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 164629705-Bromopyrimidine-2-carboxylic acid

Produkt 1

HCID 596746575-Bromopyrimidine-2-carbonyl chlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (47.4 g, 369 mmol) was added to a suspension of 5-Bromo-pyrimidine-2-carboxylic acid (50 g, 250 mmol) in dichloromethane (821 ml) at room temperature followed by 1-2 drop of dimethylformamide. The reaction mixture was stirred under nitrogen for 2 hours LCMS in methanol indicated the presence of the methyl ester and some acid. Dimethylformamide (0.2 ml) was added to the reaction mixture. The acid dissolved after 30 minutes. LCMS showed corresponding methyl ester and no starting material peak was observed. The solvent was removed and dried in vacuo to afford the crude 5-Bromo-pyrimidine-2-carbonyl chloride (55 g, 100%).

Aufarbeitung

  1. dissolutionThe acid dissolved after 30 minutes
  2. customThe solvent was removed
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0996af05180240c29e39d7292b712f9e
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735396B2

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