Ethyl 6-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-nitropyrimidine-4-carboxylate → Ethyl 5,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4-carboxylate
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:5]=[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:3]=1[N+:30]([O-])=O>N1C=CC=CC=1.[Pd]>[NH2:30][C:3]1[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:5][C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)=[N:7][C:2]=1[NH2:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
130 mg (0.30 mmol) of the compound from example 62A were initially charged in pyridine (9 ml) and then 25 mg of palladium (10% on charcoal) were added. The mixture was hydrogenated under standard hydrogen pressure at RT overnight. The reaction mixture was then filtered through Celite and the filtercake was washed with methanol. The filtrate was concentrated, methanol was added to the residue, and the solids were filtered off. The filtrate was concentrated by rotary evaporation and the residue was dried under high vacuum. This gave 51 mg (83% purity, 36% of theory) of the title compound, which were converted without further purification.