2-Methyl-5-Nitroaniline → 2-[(6-Chloro)pyrimidin-4-ylamino]-1-methyl-4-nitrobenzene

HRID 13770

Reaction equation

HRID 13770 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CO>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([NH:4][C:3]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=2[CH3:1])[CH:18]=1

Participants

6

Reactant 4

HCID 74442-Methyl-5-NitroanilineHCID 8857Ethyl AcetateHCID 709434,6-DichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 860610712-[(6-Chloro)pyrimidin-4-ylamino]-1-methyl-4-nitrobenzeneYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

2.64 g of 2-methyl-5-nitroaniline and 10.33 g of 4,6-dichloropyrimidine were stirred with heating at 110° C. for 16 hours. After air cooling, the reaction solution was dissolved in methanol. An aqueous saturated sodium hydrogen carbonate solution and ethyl acetate were added to separate the aqueous layer. The aqueous layer was further subjected to extraction with ethyl acetate twice. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain a crude product. The crude product was washed with diisopropyl ether to obtain 3.61 g of the objective compound as yellow crystals.

Workup

  1. temperatureAfter air cooling
  2. customto separate the aqueous layer
  3. extractionThe aqueous layer was further subjected to extraction with ethyl acetate twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain a crude product
  8. washThe crude product was washed with diisopropyl ether

Sources & evidence

ORD record
ord-64102c395d4244efb41b9d6bfcb88a88
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Linked notes

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