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

HRID 1068875

反応式

HRID 1068875 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7d8be0d900749e4a90bb8ed50ab8ded
出典データセット
uspto-grants-2001_06
特許番号
US06251911B1

関連ノート

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