(1,1-Dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester → 4,6-Ditert-butyl-5-hydroxy-2-pyrimidinecarboxylic acid

HRID 1742607Notes

Reaction equation

HRID 1742607 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[CH:7][N:6]=1)=[O:4]>[OH-].[Na+]>[CH3:9][C:11]([C:7]1[C:8]([OH:15])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:10]=[C:5]([C:3]([OH:2])=[O:4])[N:6]=1)([CH3:13])[CH3:12]

Participants

3

Reactant 1

HCID 67780517(1,1-Dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester

Product 1

HCID 152753184,6-Ditert-butyl-5-hydroxy-2-pyrimidinecarboxylic acidYield 143.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4,6-his (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester (500 mg) in 1N NaOH (50 mL) is heated at reflux for 1 hour. The reaction mixture is cooled, filtered, and acidified to pH 4 with 1N HCl. The resulting precipitate is collected by filtration and dried at room temperature under vacuum to give pure 4,6-bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid (430 mg); mp 200° C. dec.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. filtrationThe resulting precipitate is collected by filtration
  5. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-fce977eeebd94d9aaf2ccea1858f6074
Source dataset
uspto-grants-1994_08
Patent number
US05340815

Reaction notes

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