Sodium Hydroxide → HCID 19610613, compound

HRID 1602293Notes

Reaction equation

HRID 1602293 reaction equation
C([NH:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][NH:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[NH:13][N:12]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>O>[NH2:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][NH:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[NH:13][N:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19610560HCID 19610560, compound

Product 1

HCID 19610613HCID 19610613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.11 g (0.27 mmol) of 3-(4-acetylamino-benzylamino)-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (Example 57), 3 ml of water and 1.5 ml of 30% sodium hydroxide solution is heated at 100° C. for 4 hours. After cooling to RT, the reaction mixture is extracted with ethyl acetate and the extract is washed with brine, 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 concentrated by evaporation and the residue is recrystallized from ethyl acetate/hexane, yielding the title compound; m.p. 170-171° C.; EI-MS: (M)+ =365.

Workup

  1. temperatureAfter cooling to RT
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washthe extract is washed with brine
  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. concentrationThe product-containing fractions are concentrated by evaporation
  8. customthe residue is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-60f5e7513b1944079abf1cbdba92125b
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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