Benzenepropanoic acid → N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

HRID 1727940

反応式

HRID 1727940 の反応式
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH2:30])=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1.N1C=CC=CC=1>S(Cl)(Cl)=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH:30][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 107Benzenepropanoic acidHCID 1049PyridineHCID 6228DimethylformamideHCID 178545764-(3-Chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine

生成物 1

HCID 58981790N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

51.4 mg (0.342 mmol) of 3-phenylpropionic acid was dissolved in 1 ml of thionyl chloride. A catalytic amount of DMF was added and stirred at room temperature for 3 hours. After the solvent was evaporated under reduced pressure, 45.4 mg (0.171 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine and 1 ml of pyridine were added and stirred at 50° C. overnight. After the solvent was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with 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 title compound.

後処理

  1. additionwere added
  2. stirringstirred at 50° C. overnight
  3. customAfter the solvent was evaporated under reduced pressure
  4. additionthe reaction mixture was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. 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-355e01a8406546aab0d06881e218ff4f
出典データセット
uspto-grants-2009_02
特許番号
US07494989B2

関連ノート

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