Ammonium Hydroxide → 5-Amino-2-phenylpyrimidine-4-carboxylic acid

HRID 413688

Reaction equation

HRID 413688 reaction equation
Br[C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[OH-].[NH4+:18]>O.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:18][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 185215975-Bromo-2-phenylpyrimidine-4-carboxylic acid

Product 1

HCID 122589165-Amino-2-phenylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 8.75 g (0.0314 mole) of 5-bromo-2-phenyl-pyrimidine-4-carboxylic acid in 69 mL of concentrated ammonium hydroxide was added 0.39 g of copper (II) sulfate in 1.6 mL water. The mixture was sealed and heated to 80° C. for 6 days. After cooling to room temperature, and filtration, the solid was taken in 100 ml boiling water, filtered, cooled and acidified with acetic acid. Filtration and drying yielded 4.40 g of 5-amino-2-phenyl-pyrimidine-4-carboxylic acid as a tan solid, mp. 199-202° C.

Workup

  1. customThe mixture was sealed
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltration
  4. filtrationfiltered
  5. temperaturecooled
  6. filtrationFiltration
  7. customdrying

Sources & evidence

ORD record
ord-10cd662e71584bad9f5a0d3ea55f4f2b
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Linked notes

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