Aniline → 5-bromo-2-chloro-N-phenylpyrimidin-4-amine

HRID 548954Notes

Reaction equation

HRID 548954 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 114033895-bromo-2-chloro-N-phenylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to compound 1.1, a solution of 0.3 g (1.32 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 5 ml of acetonitrile is reacted with 0.13 ml (1.42 mmol) of aniline in the presence of 0.22 ml (1.6 mmol) of triethylamine. Purification by chromatography (silica gel, ethyl acetate/hexane with ethyl acetate 0-100%) results in 0.289 g (77% of theory) of the product.

Workup

  1. customPurification by chromatography (silica gel, ethyl acetate/hexane with ethyl acetate 0-100%)
  2. customresults in 0.289 g (77% of theory) of the product

Sources & evidence

ORD record
ord-6155ab81b7954a7da29fe3ac871c0cdd
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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