Hydrazine → 3-(2-chloro-5-methylsulfanyl-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 229407ノート

反応式

HRID 229407 の反応式
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[N:10]=[C:9](OC2C=CC(F)=CC=2F)[C:8]([C:20]([C:22]2[CH:27]=[C:26]([S:28][CH3:29])[CH:25]=[CH:24][C:23]=2[Cl:30])=O)=[CH:7][N:6]=1.[NH2:36][NH2:37]>O1CCOCC1.CCO>[Cl:30][C:23]1[CH:24]=[CH:25][C:26]([S:28][CH3:29])=[CH:27][C:22]=1[C:20]1[C:8]2[C:9](=[N:10][C:5]([O:4][C:3]3[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:2]=3[F:1])=[N:6][CH:7]=2)[NH:37][N:36]=1

参加物

4

反応物 2

HCID 9321HydrazineHCID 57758593[2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-chloro-5-methylsulfanyl-phenyl)-methanone

生成物 1

HCID 1785031753-(2-chloro-5-methylsulfanyl-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine収率 7.7%

試薬・触媒・溶媒 1

HCID 22560076Dioxan ethanol溶媒

実験手順

To a solution of [2,4-bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-chloro-5-methylsulfanyl-phenyl)-methanone (3.0 g, 5.76 mmol) in 10 mL of dioxane/EtOH (10:1) was added hydrazine (0.19 mL, 5.76 mmol) The resulting mixture was heated to reflux for 24 hours, then cooled to room temperature. The mixture was partitioned between water and ethyl acetate, and the organic layer was separated, washed twice with 1N aqueous HCl and once with wtisaturated brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (EtOAc/hexanes 5-20%) to give 180 mg of 3-(2-chloro-5-methylsulfanyl-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine, MS (M+H)=405.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customThe mixture was partitioned between water and ethyl acetate
  4. customthe organic layer was separated
  5. washwashed twice with 1N aqueous HCl and once with wtisaturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed through silica gel (EtOAc/hexanes 5-20%)

出典と根拠

ORDレコード
ord-255a4ac2d92d43039e032fa027b6afc5
出典データセット
uspto-grants-2009_07
特許番号
US07563799B2

反応ノート

読み込み中…