Dimethylformamide → 3-((7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

HRID 2036965ノート

反応式

HRID 2036965 の反応式
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][CH:13]=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.CN([CH:31]=[O:32])C>>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:31]=[O:32])=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 672169163-((7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

生成物 1

HCID 583146163-((7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile収率 37%

実験手順

To 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (69 mg, 0.24 mmol) in DMF (0.6 mL), POCl3 (130 μL, 1.4 mmol) was added at room temperature. After the addition was complete, the reaction was stirred for 1 hour at room temperature. Then, the reaction was quenched by addition to ice cold 6N NaOH. The mixture was diluted with water and the solid was collected by filtration. The solid was washed several more times with water then dried under vacuum overnight. The product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield. LCMS (M+1=318)

後処理

  1. additionAfter the addition
  2. customThen, the reaction was quenched by addition to ice cold 6N NaOH
  3. additionThe mixture was diluted with water
  4. filtrationthe solid was collected by filtration
  5. washThe solid was washed several more times with water
  6. customthen dried under vacuum overnight
  7. customThe product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield

出典と根拠

ORDレコード
ord-ec7904f84ae042659f8780f9759663a4
出典データセット
uspto-grants-2013_11
特許番号
US08575177B2

反応ノート

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