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

HRID 272633Notes

Reaction equation

HRID 272633 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)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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11.8 g (52.0 mmol) of 5-Bromo-2,4-dichloropyrimidine in 10 ml of acetonitrile at 0° C. is mixed with 4.73 ml (52.0 mmol) of aniline. The batch is stirred for 3 days at room temperature and finally concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate: 3:1 plus 1% triethylamine). 4.94 g (17.4 mmol, corresponding to 33% of theory) of the product is obtained.

Workup

  1. concentrationfinally concentrated by evaporation
  2. customThe remaining residue is purified by chromatography (hexane/ethyl acetate: 3:1 plus 1% triethylamine)
  3. custom4.94 g (17.4 mmol, corresponding to 33% of theory) of the product is obtained

Sources & evidence

ORD record
ord-bd72a4c7555d4f68a9ed14b9ffb5ab4b
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Reaction notes

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