Bromine → 5-Bromo-4,6-dichloropyrimidin-2-amine

HRID 28567

Reaction equation

HRID 28567 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[NH2:9][C:4]1[N:5]=[C:6]([Cl:8])[C:7]([Br:15])=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 655222-Amino-4,6-dichloropyrimidineHCID 517045Sodium Acetate

Product 1

HCID 6182885-Bromo-4,6-dichloropyrimidin-2-amineYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 4,6-dichloro-pyrimidin-2-yl-amine (2.46 g, 15.0 mmol) and sodium acetate (6.15 g, 75.0 mmol) in acetic acid (150 ml) was added bromine (3.24 g, 20.25 mmol) dropwise. The mixture was then stirred at 60° C. for 2 hours. Volatiles were evaporated under reduced pressure. The residue was stirred with water (500 ml) for 1 hour, filtered, and dried under reduced pressure to provide 2-amino-4,6-dichloro-5-bromo-pyrimidine (3.2 g, 88% yield) as a white solid.

Workup

  1. customVolatiles were evaporated under reduced pressure
  2. stirringThe residue was stirred with water (500 ml) for 1 hour
  3. filtrationfiltered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-16b556802db94a128af4492aaa101a92
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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