Methanol → 1-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1924242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924242
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].C([O-])=O.[NH4+:24].C1COCC1.CO>[Pd].C(Cl)Cl.CCCCCC>[NH2:24][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]

Komponenten

8

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 577430091-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

Produkt 1

HCID 577430991-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of intermediate x75 (600 mg, 2.04 mmol), ammonium formiate (644 mg, 5 eq, 10.21 mmol) and palladium on charcoal (10% wt, 109 mg, 0.1 mmol) in a 1 to 1 mixture of THF and methanol (20 ml) is allowed to react at ambient temperature for 16 hours. After filtration on celite and solvent evaporation, the crude product is purified using preparative chromatography on silicagel to furnish a crude compound which is recristallized in a mixture of CH2Cl2 and hexane to furnish 1-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one 283 as a white crystalline product (320 mg).

Aufarbeitung

  1. customto react at ambient temperature for 16 hours
  2. filtrationAfter filtration
  3. customon celite and solvent evaporation
  4. customthe crude product is purified
  5. customto furnish a crude compound which

Quellen und Nachweise

ORD-Eintrag
ord-4a3202c27cfa4072b4ca8fed789fef81
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178533B2

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