(5-aminopyridin-3-yl)[7-methyl-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone → (5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

HRID 82259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82259
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[C:17](SC)=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH3:21])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1>O1CCOCC1.[Ni]>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH3:21])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 70817471(5-aminopyridin-3-yl)[7-methyl-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

Produkt 1

HCID 70817432(5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanoneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of (5-amino-pyridin-3-yl)-(7-methyl-4-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (Preparation 231, 1.5 g, 5 mmol), Raney Ni (10 g) and NH3H2O (150 mL) in dioxane (150 mL) was refluxed for 6 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified via preparative HPLC to give (5-amino-pyridin-3-yl)-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone as a brown solid in 15% yield, 0.19 g. 1H NMR (400 MHz DMSO-d6) 3.88 (s, 3H), 5.63 (s, 2H), 7.27-7.28 (m, 1H), 8.15-8.18 (m, 2H), 8.40 (s, 1H), 8.97 (s, 1H), 9.42 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c5bc3c93e24045c5a59670d44cca645b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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