Aluminum(III) Chloride → HCID 178515990, compound

HRID 1602279Notes

Reaction equation

HRID 1602279 reaction equation
C([N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[C:11]2[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C)[CH:26]=2)=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[OH:31][C:27]1[CH:26]=[C:25]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[N:15][C:16]=3[NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[NH:8][N:9]=2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 10646832HCID 10646832, compound

Product 1

HCID 178515990HCID 178515990, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With the exclusion of air and moisture, a mixture of 44.2 mg (0.1 mmol) of 1-benzyl-4-(3-chloro-phenylamino)-3-(3-methoxy-phenyl)-pyrazolo[3,4-d]pyrimidine, 80 mg (0.6 mmol) of anhydrous aluminum chloride and 2 ml of toluene is heated under reflux for 2 hours. The reaction mixture is then poured into ice-water and extracted with ethyl acetate. The organic phase is washed with a saturated solution of sodium hydrogen carbonate in water and with brine, dried over sodium sulfate and concentrated by evaporation in vacuo. Purification of the residue by flash chromatography on silica gel (230-400 mesh) using methylene chloride and methylene chloride/methanol mixtures (19:1 and 17:3, respectively) yields the title compound; m.p. >220° C.; FAB-MS: (M+H)+ =338.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with a saturated solution of sodium hydrogen carbonate in water and with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-ba43e7e1292f42528254c29f73671548
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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