Aluminum(III) Chloride → HCID 178516088, compound

HRID 1602291Notes

Reaction equation

HRID 1602291 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]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=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]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 178491040HCID 178491040, compound

Product 1

HCID 178516088HCID 178516088, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

With the exclusion of air and moisture, a mixture of 0.5 g (1.36 mmol) of 4-(3-chloro-phenylamino)-3-(3-methoxy-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (Example 50), 0.873 g (6.55 mmol) of anhydrous aluminum chloride and 15 ml of benzene is heated at 80° C. for 9 hours. The benzene phase is then decanted off, the resinous residue is partitioned between ethyl acetate and water and the organic phase is washed with water and with a saturated solution of sodium hydrogen carbonate in water, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.06 mm using methylene chloride/methanol mixtures (50:1 and 20:1). The product-containing fractions are combined and concentrated to a volume of approx. 10 ml, the desired product crystallising out. Filtering and washing the filter residue with diethyl ether yield the title compound; m.p. 265-266° C.; EI-MS: (M)+ =352.

Workup

  1. customThe benzene phase is then decanted off
  2. customthe resinous residue is partitioned between ethyl acetate and water
  3. washthe organic phase is washed with water and with a saturated solution of sodium hydrogen carbonate in water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.06 mm
  7. concentrationconcentrated to a volume of approx. 10 ml
  8. customthe desired product crystallising out
  9. filtrationFiltering
  10. washwashing the filter residue with diethyl ether

Sources & evidence

ORD record
ord-8d70eb8205b0444fb2f1655223d416ad
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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