Cyclopropylamine → 1-([6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-one

HRID 1924305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924305
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][N:12]1[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]1=[O:20].[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:21]1([NH:24][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 577430091-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

Produkt 1

HCID 159799161-([6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-oneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one x166 (250 mg, 0.85 mmol, 1 eq) and cyclopropylamine (1 ml) is heated at 50° C. during 24 hours in THF. After cooling, a saturated aqueous solution of NaHCO3 is added and the aqueous phase is extracted with AcOEt. The combined organic layers are dried on anhydrous MgSO4, filtered of and evaporated under reduced pressure. The crude mixture is purified by preparative HPLC to yield 1-{[6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-one 285.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe aqueous phase is extracted with AcOEt
  3. dry with materialThe combined organic layers are dried on anhydrous MgSO4
  4. filtrationfiltered of and
  5. customevaporated under reduced pressure
  6. customThe crude mixture is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ea34d2f159f746889bf08cba25d24386
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178533B2

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