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

HRID 229407

Reaction equation

HRID 229407 reaction equation
[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

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57758593HCID 57758593, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-255a4ac2d92d43039e032fa027b6afc5
Source dataset
uspto-grants-2009_07
Patent number
US07563799B2

Linked notes

Loading…