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

HRID 510055Notes

Reaction equation

HRID 510055 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

HCID 66614187Ethyl 6-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-nitropyrimidine-4-carboxylate

Product 1

HCID 66614118Ethyl 5,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

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.

Workup

  1. customat RT
  2. customovernight
  3. filtrationThe reaction mixture was then filtered through Celite
  4. washthe filtercake was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. additionmethanol was added to the residue
  7. filtrationthe solids were filtered off
  8. concentrationThe filtrate was concentrated by rotary evaporation
  9. customthe residue was dried under high vacuum
  10. customThis gave 51 mg (83% purity, 36% of theory) of the title compound, which were converted without further purification

Sources & evidence

ORD record
ord-a5186b2b908145b79f283e38c29d0159
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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