Oxalyl chloride → 6-Chloro-4-pyrimidinecarboxylic acid

HRID 880329

Reaction equation

HRID 880329 reaction equation
O[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.C(Cl)(C([Cl:15])=O)=O>CCOC(C)=O.CN(C=O)C>[Cl:15][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178524636HCID 178524636, compound

Product 1

HCID 166377476-Chloro-4-pyrimidinecarboxylic acidYield 92.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 6-hydroxypyrimidine-4-carboxylic acid (6.0 g, 42.8 mmol) in EtOAc (90 mL) was added (COCl)2 (12 mL) dropwise, followed by a few drops of DMF. The mixture was stirred at 75° C. for 3 h, and then at 25° C. for 16 h. The solvent was evaporated to give the crude 6-chloropyrimidine-4-carboxylic acid (6.3 g, yield: 92.9%). 1H NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1H), 6.88 (s, 1H).

Workup

  1. waitat 25° C. for 16 h
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-92a225dc2b3c44f69e074e123efa6597
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Linked notes

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