Sodium Hydroxide → 2-Phenoxy-pyrimidine-4-carboxylic acid

HRID 2220933Notes

Reaction equation

HRID 2220933 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1)=[O:4].[OH-].[Na+]>CO>[O:11]([C:7]1[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][N:8]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 205877332-Phenoxy-pyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 219922022-Phenoxy-pyrimidine-4-carboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-phenoxy-pyrimidine-4-carboxylic acid methyl ester, 16, (1.72 g, 74.8 mmol) in methanol (50 mL) is added a 50% NaOH solution (10 mL) at room temperature. After stirring for 1.5 hours the solvent is removed in vacuo and the remaining aqueous phase is extracted with ethyl acetate. The aqueous phase can then be carefully acidified with concentrated HCl and the white solid which forms extracted twice with ethyl acetate. The organic layers are combined, dried and concentrated in vacuo to afford 0.95 g (60% yield) of the desired product as a white solid.

Workup

  1. customis removed in vacuo
  2. extractionthe remaining aqueous phase is extracted with ethyl acetate
  3. extractionthe white solid which forms extracted twice with ethyl acetate
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22ab9e1061a142b68a433d4c7c28f30f
Source dataset
uspto-grants-2008_05
Patent number
US07368455B2

Reaction notes

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