Ethyl Acetate → 4-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

HRID 496303

反応式

HRID 496303 の反応式
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][NH:32][C:33]#[N:34].C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([N:32]([C:33]#[N:34])[CH3:31])[N:3]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 119415MethylcyanamideHCID 223254954-Chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine

生成物 1

HCID 223254994-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine (0.5 g, 1.37 mmol) in dimethylformamide (6 ml) was added potassium carbonate (0.38 g, 2.73 mmol) followed by methyl cyanamide (0.31 g, 5.47 mmol). After stirring the reaction mixture at room temperature for 19 hours the reaction mixture was diluted with water (75 ml), and extracted with ethyl acetate (75 ml). The organic phase was washed with water (75 ml), followed by saturated brine (75 ml), dried over magnesium sulfate and concentrated in vacuo to afford a yellow syrup. The crude product was chromatographed an silica gel eluting with 90:10 v/v hexane:ethyl acetate to afford 0.39 g (84% yield) of the title compound as a cololess syrup.

後処理

  1. extractionextracted with ethyl acetate (75 ml)
  2. washThe organic phase was washed with water (75 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a yellow syrup
  6. customThe crude product was chromatographed an silica gel eluting with 90:10 v/v hexane

出典と根拠

ORDレコード
ord-95ad2a90ea6f404d9a72b60038922dc4
出典データセット
uspto-grants-2005_09
特許番号
US06943252B2

関連ノート

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