3-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine → HCID 178509242, Verbindung

HRID 1602229

Reaktionsgleichung

Reaktionsgleichung von HRID 1602229
C([NH:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[NH:11][N:10]=1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[NH2:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[NH:11][N:10]=1

Komponenten

4

Edukt 2

HCID 53278353-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 178509242HCID 178509242, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In order to remove residual water, some solvent is distilled off from a suspension of 75.8 g (216 mmol) of 3-benzylamino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]-pyrimidine in 1.5 liters of benzene. Then, with exclusion of moisture, the suspension is introduced into 84 g of aluminum chloride (Fluka, Buchs/Switzerland) in 500 ml of benzene. The reaction mixture is heated at 80° C. for 2.5 hours and then cooled to RT. The supernatant benzene phase is poured into 2 kg of ice-water (leaving behind a green, oily residue) and the solid that precipitates is filtered with suction and rinsed thoroughly with water (→K1). Using a rotary evaporator, the benzene is evaporated off from the filtrate, and the aqueous phase that remains is added, together with 1 kg of ice, to the green, oily residue and hydrolysis is carried out for 2 hours at 40° C. The crystalline product is filtered with suction and rinsed with water (→K2). K1 and K2 are taken up in 1 liter of methanol, acidified with 4N aqueous HCl and partially concentrated by evaporation. Water is added and the methanol is evaporated off completely. The crystals are filtered off and rinsed with water. The same purification procedure is repeated with semi-saturated Na2CO3 solution/methanol and water/methanol. Stirring at 50° C. in methanol, precipitation with diethyl ether, filtering and drying yield 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 232-234° C.; TLC: Rf =0.50 (ethyl acetate).

Aufarbeitung

  1. customIn order to remove residual water
  2. temperaturecooled to RT
  3. customleaving behind a green, oily residue) and the solid
  4. customthat precipitates
  5. filtrationis filtered with suction
  6. washrinsed thoroughly with water (→K1)
  7. customa rotary evaporator
  8. customthe benzene is evaporated off from the filtrate
  9. additionthe aqueous phase that remains is added, together with 1 kg of ice
  10. customto the green, oily residue and hydrolysis
  11. filtrationThe crystalline product is filtered with suction
  12. washrinsed with water (→K2)
  13. concentrationpartially concentrated by evaporation
  14. additionWater is added
  15. customthe methanol is evaporated off completely
  16. filtrationThe crystals are filtered off
  17. washrinsed with water
  18. customThe same purification procedure
  19. customprecipitation with diethyl ether
  20. filtrationfiltering
  21. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b4ec575f8ee3417ba56b99314c481103
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981533

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