Pyridine → 4-(3-Chlorophenyl)-3-ethoxycarbonyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

HRID 24616ノート

反応式

HRID 24616 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]([C:20]([O:22]CC3C=CC=CC=3)=O)=[C:18]([CH3:30])[NH:17][C:16]([O:31]C)=[N:15]2)[CH:11]=[CH:12][CH:13]=1.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(OCC)(=O)C>[C:3]1([CH:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:6][NH:1][C:20]([C:19]2[CH:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=3)[N:15]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:16](=[O:31])[NH:17][C:18]=2[CH3:30])=[O:22])[CH:14]=[CH:19][CH:18]=[CH:30][CH:2]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22570191Benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate

生成物 1

HCID 207589254-(3-Chlorophenyl)-3-ethoxycarbonyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

10 ml of pyridine was added to a mixture of 512 mg (1.38 mmol) of benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate and 180 mg (1.66 mmol) of ethyl chloroformate, and they were stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, then washed with water and saturated aqueous sodium chloride solution and concentrated under reduced pressure. The product was dissolved in a mixture of 5 ml of methanol and 5 ml of THF. 3 N hydrochloric acid was added to the obtained solution, and they were stirred at room temperature for 10 minutes. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the crude title compound.

後処理

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe product was dissolved in a mixture of 5 ml of methanol and 5 ml of THF
  4. addition3 N hydrochloric acid was added to the obtained solution, and they
  5. stirringwere stirred at room temperature for 10 minutes
  6. concentrationAfter the concentration under reduced pressure
  7. additionthe reaction mixture was diluted with ethyl acetate
  8. washwashed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

出典と根拠

ORDレコード
ord-ec8766218c474afca8958342d0002960
出典データセット
uspto-grants-2005_02
特許番号
US06855716B2

反応ノート

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