Cesium carbonate → HCID 11202164, compound

HRID 899318Notes

Reaction equation

HRID 899318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:10]=[C:11]3[C:16]([OH:17])=[N:15][C:14]([CH2:18][CH3:19])=[N:13][C:12]=23)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:33]([CH2:37]I)([F:36])([F:35])[F:34]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:10]=[C:11]3[C:16](=[O:17])[N:15]([CH2:37][C:33]([F:36])([F:35])[F:34])[C:14]([CH2:18][CH3:19])=[N:13][C:12]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 178437763HCID 178437763, compound

Product 1

HCID 11202164HCID 11202164, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-ethyl-2H-pyrazolo[4,3-d]pyrimidin-7-ol (I-3A-1a, 15 mg, 0.039 mmol), Cs2CO3 (52 mg, 0.16 mmol) and CF3CH2I (39 μl, 0.4 mmol) in DMF (1 ml) was stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature, quenched with saturated aqueous sodium chloride, and extracted with ethyl acetate (2×). The combined extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by radial chromatography (Chromatotron) using a 1 mm silica gel plate and a solvent gradient of 25% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to provide the desired product, 3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-ethyl-6-(2,2,2-trifluoroethyl)-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one 3A-1 (11 mg): MS 467.4 (M+1); 1H NMR (400 MHz, CD2Cl2): δ 7.57-7.43 (m, 4H), 7.44-7.40 (m, 2H), 7.34-7.30 (m, 2H), 5.00-4.80 (br m, 2H), 2.87 (q, J=7.1 Hz, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with saturated aqueous sodium chloride
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined extracts were washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by radial chromatography (Chromatotron)

Sources & evidence

ORD record
ord-b65c5f95f010451d8afc2f640f3dee65
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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