Dimethylformamide → 5-Bromopyrimidine-2-carbonyl chloride

HRID 1253614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253614
[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 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (1.45 g, 11.1 mmol) was added to a suspension of 5-Bromo-pyrimidine-2-carboxylic acid (1.5 g, 7.4 mmol) in dichloromethane (50 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 and all of 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 (1.6 g).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2480056584af4cd4ac0dc7b2c9507d83
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455496B2

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