Dimethylformamide → 5-Bromopyrimidine-2-carbonyl chloride

HRID 1027699Notes

Reaction equation

HRID 1027699 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 596746575-Bromopyrimidine-2-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-0996af05180240c29e39d7292b712f9e
Source dataset
uspto-grants-2014_05
Patent number
US08735396B2

Reaction notes

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