Triethylsilane → HCID 178454101, Verbindung

HRID 707260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707260
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3[N:17]=[C:18](SC)[N:19]=[CH:20][C:15]=3[C:14]([CH3:24])([CH3:23])[C:13]2=[O:25])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C>O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:9][C@H:10]([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[C:14]([CH3:24])([CH3:23])[C:13]2=[O:25])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 12052TriethylsilaneHCID 178503401HCID 178503401, Verbindung

Produkt 1

HCID 178454101HCID 178454101, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl(trans-3-(5,5-dimethyl-2-(methylthio)-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate, INTERMEDIATE 63, (0.9 g, 2.378 mmol) in dry tetrahydrofuran (10 mL) was added cautiously palladium 10 wt. % on activated carbon (0.051 ml, 0.476 mmol) followed by triethylsilane (3.04 ml, 19.02 mmol). The mixture was stirred for 15 minutes under nitrogen atmosphere, filtered, and filtrate concentrated to give tert-butyl(trans-3-(5,5-dimethyl-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate. The crude tert-butyl(trans-3-(5,5-dimethyl-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate was redissolved in dioxane (10 mL) and treated with 4N HCl in dioxane (10 mL). After 30 minutes the reaction mixture was evaporated to dryness under reduced pressure to give the desired crude product 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride (0.55 g, 2.047 mmol, 86% yield). The product was used in next step without further purification. m/z: 233.0 (M+1-HCl).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationfiltrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-93149cffd59241ccbfb2f5190598ddec
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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