Aluminum(III) Chloride → HCID 178420487, compound

HRID 1602216Notes

Reaction equation

HRID 1602216 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C([N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:15]2[C:14]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:13]1)C1C=CC=CC=1>C1C=CC=CC=1.O>[C:29]1([NH:28][C:14]2[C:15]3[C:16](=[N:17][CH:18]=[N:19][C:20]=3[NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:12][N:13]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 10763097HCID 10763097, compound

Product 1

HCID 178420487HCID 178420487, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

With the exclusion of air and moisture, there is added to a suspension of 203 mg of AlCl3 in 2.5 ml of absolute benzene a solution of 100 mg of 1-benzyl-3,4-diphenylamino-pyrazolo[3,4-d]pyrimidine in 2.5 ml of absolute benzene. The reaction mixture is stirred for 1.5-2 hours at 50° C. until, according to thin-layer chromatography, no starting material remains and is then stirred in approx. 30 ml of water. The precipitate is filtered off and dissolved in ethyl acetate. The ethyl acetate phase is washed several times with 5% aqueous sodium hydrogen carbonate solution and then with saturated sodium chloride solution, dried and concentrated to dryness by evaporation. The residue is crystallized from ethyl acetate/hexane, yielding 3,4-diphenylamino-1H-pyrazolo[3,4-d]pyrimidine in the form of colorless crystals, m.p. 263-264° C., FAB-MS: (M+H)+ =303 (C17H14N6).

Workup

  1. filtrationThe precipitate is filtered off
  2. dissolutiondissolved in ethyl acetate
  3. washThe ethyl acetate phase is washed several times with 5% aqueous sodium hydrogen carbonate solution
  4. dry with materialwith saturated sodium chloride solution, dried
  5. concentrationconcentrated to dryness by evaporation
  6. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f01a9dd9372c43d29fd442f70b68e754
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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