Hydrochloric Acid → 2-Phenylpyrimidine-5-carboxylic acid

HRID 219636Notes

Reaction equation

HRID 219636 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-].C1COCC1.Cl>CO.O>[C:11]1([C:8]2[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11206661Methyl 2-phenylpyrimidine-5-carboxylate

Product 1

HCID 7473892-Phenylpyrimidine-5-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-phenyl-pyrimidine-5-carboxylic acid methyl ester (3.15 g) and LiOH (0.71 g) in a mixture of MeOH, THF and water (1:1:1 in volume, 120 mL) is stirred at room temperature overnight. MeOH and THF are evaporated off to give an aqueous solution. The aqueous solution is acidified with 5% hydrochloric acid to adjust pH to between 2.5 and 3. The precipitate is filtered off and washed with water, dried in vacuo to yield 2.94 g (˜100%) of 2-phenyl-pyrimidine-5-carboxylic acid as a solid. MS: 201 (M+H).

Workup

  1. customMeOH and THF are evaporated off
  2. customto give an aqueous solution
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-00690f4623564ea2baf1db22e539bbd6
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…