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

HRID 13770

反応式

HRID 13770 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64102c395d4244efb41b9d6bfcb88a88
出典データセット
uspto-grants-2010_06
特許番号
US07728131B2

関連ノート

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