Cesium carbonate → HCID 11247638, compound

HRID 899316Notes

Reaction equation

HRID 899316 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:10]=[C:11]3[C:16]([OH:17])=[N:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.I[CH2:26][C:27]([F:30])([F:29])[F:28].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:10]=[C:11]3[C:16](=[O:17])[N:15]([CH2:26][C:27]([F:30])([F:29])[F:28])[CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 178517945HCID 178517945, compound

Product 1

HCID 11247638HCID 11247638, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-ol (I-2A-1b: 1.20 g, 3.36 mmol), 2-iodo-1,1,1-trifluoroethane (705 mg, 3.36 mmol) and Cs2CO3 (2.19 g, 6.72 mmol) in DMF (20 ml) was heated at 100° C. for 17 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic solution was washed with saturated aqueous NaCl, dried, and concentrated in vacuo. The crude residue was purified via a Shimadzu HPLC system using a Waters XTERRA C18 50×50 mm column and a mixture of two solvent systems (0.1% NH4OH/CH3CN and H2O/0.1% NH4OH) to give the title compound 2A-1 (300 mg, 20%) as an amorphous solid: +ES MS (M+1) 439.1; 1H NMR (CDCl3) δ 7.87 (s, 1H), 7.54-7.30 (m, 8H), 4.7 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic solution was washed with saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via a Shimadzu HPLC system
  6. additiona mixture of two solvent systems (0.1% NH4OH/CH3CN and H2O/0.1% NH4OH)

Sources & evidence

ORD record
ord-469f54e7d69a4f70a6b5fb3e6fe9de40
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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