Aniline → 4-Anilino-2,5-dichloropyrimidine

HRID 1471956Notes

Reaction equation

HRID 1471956 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([Cl:16])=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:8][C:9]1[N:14]=[C:13]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12]([Cl:16])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 187680474-Anilino-2,5-dichloropyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Aniline (205 mg, 2.2 mmol) and 2,4,5-Trichloropyrimidine (500 mg, 2.7 mmol) in 5 mL of Ethanol, was added 500 mg of Potassium carbonate. The reaction mixture was stirred at room temperature for 2 hours. Solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography with 10% Ethyl Acetate in Heptane to yield the desired product as an oil (370 mg, 70% yield).

Workup

  1. customSolvent was removed under reduced pressure
  2. customThe residue was purified by silica gel flash chromatography with 10% Ethyl Acetate in Heptane

Sources & evidence

ORD record
ord-cb698f8c28da4e7285bed9e818da7eb2
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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