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
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]1Participants
4
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.