Ethanol → 4-(2-Bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acid

HRID 650622Notes

Reaction equation

HRID 650622 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[N:8][C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5])C.C(O)C>O>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([CH3:12])[N:8]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 22831713Ethyl-2-methyl-4-(2-bromophenyl)-pyrimidine-5-carboxylate

Product 1

HCID 217124084-(2-Bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.3 g (25.8 mmol) 4-(2-bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acid ethyl ester in 10 ml ethanol 1.55 g (38.6 mmol) NaOH in 20 ml H2O was added. After stirring for 1 hr., the reaction mixture was washed with 100 ml diethylether. The pH of the aqueous phase was adjusted to 1 with 25% HCl and than extracted twice with 200 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtrated and evaporated to give 7.0 g (92%) 4-(2-bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acid as a pale yellow foam.

Workup

  1. wash, the reaction mixture was washed with 100 ml diethylether
  2. extractionthan extracted twice with 200 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-8ec6ba57712c4a44a89b765ef0c60b25
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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