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Ammonia → 2-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 1168283
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1168283
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]#[N:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:9].[NH2:20][CH2:19][C:17]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[C:10]([NH:9][CH2:8][CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:18]=1
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Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 101593916-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrileHCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 222AmmoniaHCID 229486282-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineAusbeute 153,7 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 6-[(2,2-diphenylethyl)amino]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carbonitrile (5.70 g, 13.18 mmol) (Preparation 5) in ethanol (200 ml) saturated with ammonia gas was treated with Pearlman's catalyst (1.00 g), pressurised to 414 kPa (60 psi) with hydrogen in a sealed vessel and stirred at room temperature for 30 hours. The suspension was filtered through a pad of Arbocel (trade mark) and the solvent was removed under reduced pressure. The residue was twice azeotroped from dichloromethane and then purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) to afford the title compound (4.34 g).

Aufarbeitung

  1. filtrationThe suspension was filtered through a pad of Arbocel (trade mark)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was twice azeotroped from dichloromethane
  4. custompurified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-cf49ce7076a340d0a7eb2f898890c951
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06624158B2

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