Ammonium Hydroxide → 5-Amino-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid

HRID 1915900Notes

Reaction equation

HRID 1915900 reaction equation
Br[C:2]1[C:3]([C:15]([OH:17])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6][CH:7]=1.[OH-].[NH4+:19]>[O-]S([O-])(=O)=O.[Cu+2]>[NH2:19][C:2]1[C:3]([C:15]([OH:17])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 821686735-Bromo-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid

Product 1

HCID 666525805-Amino-2-(2-fluorophenyl)pyrimidine-4-carboxylic acidYield 53%

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Conditions

Temperature
110 °C

Procedure

CuSO4 (with 5H2O, 65 mg) was added to a mixture of the above made 5-bromo-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid (770 mg, 2.59 mmol) and 28% aqueous ammonium hydroxide (12 ml). The reaction was heated in a microwave reactor at 110° C. for 30 min. It was cooled to RT and concentrated in vacuo. The residue was diluted with 1N HCl (20 mL) and extracted with EtOAc 3×. Combined organic extracts were dried over sodium sulfate and filtered and concentrated to give 5-amino-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid (320 mg, 53%).

Workup

  1. temperatureIt was cooled to RT
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 1N HCl (20 mL)
  4. extractionextracted with EtOAc 3×
  5. dry with materialCombined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a3af1c28561745f6b9c400970210c5ab
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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