Acetic Acid → 4-(3-chloro-phenylamino)-3-(4-phenyl-benzylamino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068900Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.[C:19]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CN1C(=O)N(C)CC1.CO>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][CH2:25][C:22]4[CH:23]=[CH:24][C:19]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:20][CH:21]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under a nitrogen atmosphere, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1 H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 273 mg (1.5 mmol) of biphenyl-4-carbaldehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) at RT for 1 hour. 440 mg (7 mmol) of NaCNBH3 are then added and the reaction mixture is heated to 50° C. After 15 hours a further 440 mg of NaCNBH3 are added and the reaction mixture is stirred at boiling temperature for 15 hours, then poured into 0.6 liter of a 1% aqueous K2B4O7.4H2O solution and stirred overnight to complete the reaction. The precipitated product is filtered off and washed with water. Heating in 20 ml of ethanol and filtration yield 4-(3-chloro-phenylamino)-3-(4-phenyl-benzylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 250-252° C.; HPLC: tRet(grad20-100/20=14.1; FAB-MS: (M+H)+=427.

Workup

customfor 15 hours
stirringstirred overnight
customthe reaction
filtrationThe precipitated product is filtered off
washwashed with water
temperatureHeating in 20 ml of ethanol
filtrationfiltration

Sources & evidence

ORD record: ord-fb511f982cfe4d5eaec7316b198d0247
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251911B1

Reaction notes

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