Dimethylformamide → 7-(Benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624731ノート

反応式

HRID 624731 の反応式
[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:34]=[O:35])C>>[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:34]=[O:35])=[C:13]2[N:12]=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 583150077-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine

生成物 1

HCID 583138967-(Benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde収率 83%

実験手順

To 7-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine (4.1 g, 11.3 mmol) in DMF (42 mL), POCl3 (6.3 mL, 67.6 mmol) was added dropwise at room temperature. After the addition was complete, the reaction was stirred for 3 hours at room temperature. Then, the reaction was quenched by slow 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, 7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was collected as a solid in 83% yield. LCMS (M+1=395)

後処理

  1. additionAfter the addition
  2. customThen, the reaction was quenched by slow 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, 7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was collected as a solid in 83% yield

出典と根拠

ORDレコード
ord-f50c4256c3264a8f97a948a9dfc3f329
出典データセット
uspto-grants-2016_04
特許番号
US09303033B2

反応ノート

読み込み中…