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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 510055
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 510055
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a5186b2b908145b79f283e38c29d0159
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096592B2

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