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

HRID 1602223

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e23e397384e44c0baf234b0b8c923f72
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981533

Linked notes

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