Ethyl Acetate → 3-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1602223

Reaktionsgleichung

Reaktionsgleichung von HRID 1602223
[CH2:1]([NH:8][C:9]1[C:13]([C:14]#[N:15])=[C:12]([N:16]=[CH:17][N:18](C)C)[NH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)N.C([O-])(O)=O.[Na+].C(OCC)(=O)C>CO>[CH2:1]([NH:8][C:9]1[C:13]2[C:12](=[N:16][CH:17]=[N:18][C:14]=2[NH:15][C:28]2[CH:27]=[CH:25][CH:24]=[C:23]([Cl:22])[CH:29]=2)[NH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 53832654N'-(3-benzylamino-4-cyano-1H-pyrazol-5-yl)-N,N-dimethylformamidine

Produkt 1

HCID 53278353-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

With the exclusion of moisture, 79.2 g (295 mmol) of N'-(3-benzylamino-4-cyano-1H-pyrazol-5-yl)-N,N-dimethylformamidine are suspended in 700 ml of methanol; 60.6 g (369 mmol) of 3-chloro-aniline hydrochloride are added and the reaction mixture is boiled under reflux for 22 hours. The resulting yellow reaction solution is cooled to ≈50° C. and poured onto 2 liters of ice-water, 200 ml of saturated NaHCO3 solution and 1 liter of ethyl acetate. The aqueous phase is separated off and extracted twice with ethyl acetate. The organic phases are washed twice with water, saturated NaHCO3 solution, water and brine, dried (Na2SO4) and concentrated by evaporation to a residual volume of ≈1.5 liters. Inoculation and dilution with 300 ml of diethyl ether yield crystalline 3-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 214-217° C.; TLC: Rf =0.29 (ethyl acetate:hexane=1:1).

Aufarbeitung

  1. temperatureunder reflux for 22 hours
  2. customThe aqueous phase is separated off
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phases are washed twice with water, saturated NaHCO3 solution, water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation to a residual volume of ≈1.5 liters

Quellen und Nachweise

ORD-Eintrag
ord-e23e397384e44c0baf234b0b8c923f72
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981533

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