Aluminum(III) Chloride → HCID 178515919, compound

HRID 1602283Notes

Reaction equation

HRID 1602283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([C:18]4[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 178489151HCID 178489151, compound

Product 1

HCID 178515919HCID 178515919, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

With the exclusion of air and moisture, a mixture of 0.442 g (1.2 mmol) of 4-(3-chloro-phenylamino)-3-(4-methoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidine [see Example 34], 1.16 g (8.7 mmol) of anhydrous aluminum chloride and 20 ml of benzene is heated under reflux for 45 minutes. The reaction mixture is then poured into ice-water, filtered and washed with water and the filter residue is partitioned between a 5% solution of sodium hydrogen carbonate in water and ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated in vacuo. A small amount of hexane is added and the desired product precipitates. Washing with hexane and purification of the crude product by flash chromatography on silica gel (230-400 mesh) using an ethyl acetate/hexane mixture (7:3) yield the title compound; m.p. >220° C.; MS: (M)+ =337.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 45 minutes
  3. filtrationfiltered
  4. washwashed with water
  5. customthe filter residue is partitioned between a 5% solution of sodium hydrogen carbonate in water and ethyl acetate
  6. washThe organic phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. additionA small amount of hexane is added
  10. customthe desired product precipitates
  11. washWashing with hexane and purification of the crude product by flash chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-50d9c1937e384c7db26c62209e3ee6cb
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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