HCID 178526611, compound → HCID 178507540, compound

HRID 1602255Notes

Reaction equation

HRID 1602255 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Ni].CO.C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 178526611HCID 178526611, compound

Product 1

HCID 178507540HCID 178507540, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the presence of 30 mg of Raney nickel, 110 mg (0.30 mmol) of 3-(3-nitro-phenyl)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine are hydrogenated in 3 ml of methanol and 3 ml of THF. The catalyst is filtered off, then 15 g of silica gel are added to the filtrate, which is then concentrated by evaporation. Application of the powder to a silica gel column, elution with methylene chloride/ethanol (15:1) and stirring of the crude product with diethyl ether/hexane yield 3-(3-amino-phenyl)-4-(3-chloro-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine; m.p. 264-266° C.; TLC: Rf =0.45 (methylene chloride/methanol 10:1); HPLC: TRet (Grad20-100)=9.7.

Workup

  1. filtrationThe catalyst is filtered off
  2. addition15 g of silica gel are added to the filtrate, which
  3. concentrationis then concentrated by evaporation
  4. washApplication of the powder to a silica gel column, elution with methylene chloride/ethanol (15:1)

Sources & evidence

ORD record
ord-de65481f771b42c7b7c3073b2db127f7
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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