(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile → (R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44839

Reaktionsgleichung

Reaktionsgleichung von HRID 44839
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([CH2:21][C:22]#[N:23])[N:18]=[CH:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:24])[C:8](=[O:25])[C@H:7]2[CH2:26][CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.O=[Pt]=O>[NH2:23][CH2:22][CH2:21][C:19]1[N:18]=[CH:17][N:16]([C:13]2[N:12]=[CH:11][C:10]3[N:9]([CH3:24])[C:8](=[O:25])[C@@H:7]([CH2:26][CH3:27])[N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:15]=3[N:14]=2)[CH:20]=1

Komponenten

4

Edukt 1

HCID 58405740(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile

Produkt 1

HCID 58405893(R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile (Example 35, 0.08 g, 0.218 mmol) and PtO2 (40 mg) were suspended in 2 mL of EtOAc and the resulting mixture was stirred under an atmosphere of hydrogen (1 atm, balloon) for 18 h. The resulting solution was filtered through Celite, concentrated, then purified by preparative HPLC to give the title compound (34 mg). LCMS: 370.1 m/z (M+H)+; ret. Time: 4.09 (Analytical Method C).

Aufarbeitung

  1. filtrationThe resulting solution was filtered through Celite
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-375633b2085a4bb3a7a0ebd80fb12d18
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541418B2

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