4-(2,3-Dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine → 4-(2,3-Dihydroindol-1-yl)-6-(4-amino-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369711Notes

Reaction equation

HRID 369711 reaction equation
[N:1]1([C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>[Ni].CO.C1COCC1>[N:1]1([C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 232824614-(2,3-Dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 232824604-(2,3-Dihydroindol-1-yl)-6-(4-amino-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

400 mg of 4-(2,3-dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine (Example 6) are hydrogenated with 150 mg of Raney nickel in methanol/THF (35:20) at RT and normal pressure for 10 hours. The catalyst is filtered off and the solution is concentrated by evaporation. The residue is dissolved in THF and the product is precipitated by the addition of hexane. 4-(2,3-Dihydroindol-1-yl)-6-(4-amino-phenyl)-7H-pyrrolo[2,3-d]pyrimidine is obtained in the form of a colorless powder. M.p. >300° C.; FAB-MS: (M+H)+ =328 (corresponds to C20H17N5); Rf value (toluene-acetone--4:6)=0.21.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution is concentrated by evaporation
  3. dissolutionThe residue is dissolved in THF
  4. customthe product is precipitated by the addition of hexane

Sources & evidence

ORD record
ord-9847cfbf95c440c5bd12226c65517c47
Source dataset
uspto-grants-2000_10
Patent number
US06140317

Reaction notes

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