Water → 2-Methoxypyrimidine-5-carboxylic acid

HRID 488457Notes

Reaction equation

HRID 488457 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([O:11]C)=[O:10])=[CH:5][N:4]=1.O.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12627753Methyl 2-methoxypyrimidine-5-carboxylate

Product 1

HCID 64866182-Methoxypyrimidine-5-carboxylic acidYield 69.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-methoxypyrimidine-5-carboxylate (944 mg) (Z. Budesinsky and J. Vavrina, Collect. Czech. Chem. Commun. 37 (1972)1721-1733) in dioxan (33 ml)/water (33 ml) was treated with 2N NaOH (3.37 ml), left overnight and evaporated to low volume. The residue was taken up in water (30 ml), the pH adjusted to 2 by addition of 2N HCl and the mixture extracted with EtOAc (4×30 ml). The EtOAc was dried and evaporated to give the title compound as a white solid (605 mg) 1HNMR δ(DMSO) 4.00(3H,s), 9.03(2H,s).

Workup

  1. customevaporated to low volume
  2. additionthe pH adjusted to 2 by addition of 2N HCl
  3. extractionthe mixture extracted with EtOAc (4×30 ml)
  4. dry with materialThe EtOAc was dried
  5. customevaporated

Sources & evidence

ORD record
ord-90b8e6275a244adcad71c06ce1726ac4
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Reaction notes

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