Aniline → HCID 10763097, compound

HRID 1602219Notes

Reaction equation

HRID 1602219 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16](Cl)=[C:11]2[C:10]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:11]2[C:10]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 10592935HCID 10592935, compound

Product 1

HCID 10763097HCID 10763097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of 1-benzyl-4-chloro-3-phenylamino-pyrazolo[3,4-d]pyrimidine is suspended in 8 ml of ethanol; 27 ml of aniline are added thereto and, under nitrogen, the reaction mixture is heated under reflux for 2.5 hours until, according to thin-layer chromatography, all the starting material has disappeared. The reaction mixture is concentrated to dryness by evaporation, the residue is suspended in water and the pH is adjusted to pH 8.5-9 with 0.1N NaOH. Extraction is then carried out with ethyl acetate and the ethyl acetate phase is then dried and concentrated by evaporation. The crude product is chromatographed on silica gel, mixtures of toluene/ethyl acetate being used as eluant. Product-containing column fractions are stirred with cyclohexane/hexane, yielding colorless crystals of 1-benzyl-3,4-diphenylamino-pyrazolo[3,4-d]pyrimidine; FAB-MS: (M+H)+ =393 (C24H20N6).

Workup

  1. temperatureunder nitrogen, the reaction mixture is heated
  2. temperatureunder reflux for 2.5 hours until,
  3. concentrationThe reaction mixture is concentrated to dryness by evaporation
  4. extractionExtraction
  5. dry with materialthe ethyl acetate phase is then dried
  6. concentrationconcentrated by evaporation
  7. customThe crude product is chromatographed on silica gel, mixtures of toluene/ethyl acetate being
  8. additionProduct-containing column fractions

Sources & evidence

ORD record
ord-e251460b32d14be7bea7f547d75ba431
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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