Lithium Hydroxide → 2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid

HRID 2381906Notes

Reaction equation

HRID 2381906 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]=[C:13]([F:17])[CH:12]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-]>CO>[F:17][C:13]1[CH:12]=[C:11]([C:8]2[N:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 45073367HCID 45073367, compound

Product 1

HCID 450733632-(3-Fluorophenyl)pyrimidine-5-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid methyl ester (1.76 g, 7.58 mmol) in anhydrous MeOH (35 mL) is added LiOH (0.38 g, 15.9 mmol) and the reaction mixture is stirred at rt overnight. The mixture is concentrated in vacuo and the residue is partitioned between EtOAc and 3 N aqueous HCl (7.6 mL). The mixture is extracted with EtOAc and the organic layer is washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (1.62 g, 98%) as a solid. MS: 219 (M+H).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is partitioned between EtOAc and 3 N aqueous HCl (7.6 mL)
  3. extractionThe mixture is extracted with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-135f082c21214c6db049705e0cdaa9fe
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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