Aluminum(III) Chloride → CGP-59326

HRID 2293121Notes

Reaction equation

HRID 2293121 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[NH:5][C:6]1[C:7]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12](CC3C=CC=CC=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[NH:5][C:6]1[C:7]2[C:14]([CH3:15])=[C:13]([CH3:16])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 10808671HCID 10808671, compound

Product 1

HCID 9816954CGP-59326

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g (2.76 mmol) of 4-(m-chloroanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine and 2.57 g (19.32 mmol) of AlCl3 are heated at reflux in 20 ml of toluene for 2 hours, until all starting material has disappeared in a TLC. The reaction solution is cooled to RT, poured onto ice-water and stirred at 0° C. for 2 hours. The precipitate is filtered off with suction and dissolved in hot ethyl acetate. The ethyl acetate solution is washed twice each with 5% sodium hydrogen carbonate solution and sat. NaCl solution, is dried and is concentrated by evaporation. The residue is crystallised from ethyl acetate/hexane, yielding 4-(m-chloroanilino)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine in the form of colourless crystals having a melting point of 239°-240° C.

Workup

  1. additionpoured onto ice-water
  2. filtrationThe precipitate is filtered off with suction
  3. dissolutiondissolved in hot ethyl acetate
  4. washThe ethyl acetate solution is washed twice each with 5% sodium hydrogen carbonate solution and sat. NaCl solution
  5. customis dried
  6. concentrationis concentrated by evaporation
  7. customThe residue is crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bed731b8dce6437c993f053ec6941c11
Source dataset
uspto-grants-1997_11
Patent number
US05686457

Reaction notes

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