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

HRID 229407노트

반응식

HRID 229407 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 22560076Dioxan ethanol용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-255a4ac2d92d43039e032fa027b6afc5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563799B2

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