Sodium hydride → 5-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 1896086ノート

反応式

HRID 1896086 の反応式
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[CH:12]([S:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])(=[O:17])=[O:16])([CH3:14])[CH3:13].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[S:15]([CH:12]([CH3:14])[CH3:13])(=[O:17])=[O:16])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidineHCID 126463662-(Propane-2-sulfonyl)aniline

生成物 1

HCID 583753895-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5,7-dichloro-pyrazolo[1,5-a]pyrimidine (1.0 mmol) and 2-(isopropylsulfonyl)aniline(1.0 mmol) in 5 mL of DMF, was added carefully NaH (24 mg). The resulting suspension was stirred at 50° C. for 2 hours. After cooling at RT and careful quenching (ice), water was added and the mixture was extracted with EtOAc. The organic layers were collected, dried (Na2SO4), filtrated and concentrated. The residue was purified over SiO2 column chromatography (eluent: 9:1 Hexane:EtOAc), to give the desired 5-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine. MS (ES+): 351.06 (M+1)+.

後処理

  1. temperatureAfter cooling at RT
  2. customcareful quenching (ice), water
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layers were collected
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe residue was purified over SiO2 column chromatography (eluent: 9:1 Hexane:EtOAc)

出典と根拠

ORDレコード
ord-5fe06219ef4442ba80f0705b978998ec
出典データセット
uspto-grants-2013_08
特許番号
US08518931B2

反応ノート

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