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

HRID 1068875

반응식

HRID 1068875 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

With the exclusion of moisture, 79.2 g (295 mmol) of N′-(3-benzylamino-4-cyano-1 H-pyrazol-5-yl)-N,N-dimethyl-formamidine are suspended in 700 ml of methanol; 60.6 g (369 mmol) of 3-chloro-aniline hydrochloride are added and the mixture is boiled under reflux for 22 hours. The resulting yellow reaction solution is cooled to 50° C. and poured into 2 liters of ice-water, 200 ml of sat. 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, sat. NaHCO3 solution, water and brine, dried (Na2SO4) and concentrated by evaporation to a residual volume of ≈1.5 liters. Seeding 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).

후처리

  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, sat. NaHCO3 solution, water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation to a residual volume of ≈1.5 liters

출처 및 근거

ORD 기록
ord-d7d8be0d900749e4a90bb8ed50ab8ded
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251911B1

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