7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine → 7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 82144

Reaktionsgleichung

Reaktionsgleichung von HRID 82144
[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:16]2[N:17]=[CH:18][N:19]=[C:20](Cl)[C:15]=2[CH:14]=[CH:13]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.N.[Pd]>[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:16]2[N:17]=[CH:18][N:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1)[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

5

Edukt 1

HCID 866720787-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 708176697-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 222AmmoniaLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

Palladium (10% on carbon, 18 g) was added to 7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (182 g, 558 mmol) (see Preparation 1) in ethanol (900 mL) and concentrated ammonia solution (100 mL) and hydrogenated (60 psi, 20° C.) for 18 hours. The reaction mixture was filtered through Arbocel™ and the filtrate was evaporated in vacuo. Diethyl ether (300 mL) was added to the residue and the mixture was filtered. The filtrate was evaporated in vacuo to afford the title compound as an orange oil in 94% yield, 162.7 g.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Arbocel™
  2. customthe filtrate was evaporated in vacuo
  3. additionDiethyl ether (300 mL) was added to the residue
  4. filtrationthe mixture was filtered
  5. customThe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4597911af295450aaca7933c8a0f5f58
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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