2-[5-Fluoro-1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-nitro-4,6-pyrimidinediamine → 2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine

HRID 1777806Notes

Reaction equation

HRID 1777806 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([N+:18]([O-])=O)=[C:13]([NH2:21])[N:12]=3)=[N:9][N:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:5]2=[N:6][CH:7]=1>N1C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:21])[N:12]=3)=[N:9][N:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 580656012-[5-Fluoro-1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-nitro-4,6-pyrimidinediamine

Product 1

HCID 580656032-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

In pyridine (30 ml), 378 mg (0.949 mmol) of the compound from Example 7A were introduced and then 143 mg (0.135 mmol) of palladium (10% on carbon) were added. The mixture was hydrogenated overnight at RT under standard hydrogen pressure. The suspension was then filtered through kieselguhr and the filtercake was washed with ethanol. The filtrate was concentrated and yielded 233 mg (81% purity, 51% of theory) of the desired compound, which was reacted without further purification.

Workup

  1. filtrationThe suspension was then filtered through kieselguhr
  2. washthe filtercake was washed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-14aa906e2a884d88a32cf9d8b569a6bc
Source dataset
uspto-grants-2016_02
Patent number
US09266885B2

Reaction notes

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