Potassium Carbonate → (R)-3-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-2-yl)oxazolidin-2-one

HRID 44846

Reaktionsgleichung

Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.[O:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[N:28]4[CH2:29][CH2:30][O:26][C:27]4=[O:31])[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 0.11 g, 0.271 mmol), oxazolidin-2-one (35 mg, 0.406 mmol), CuI (10 mg, 0.054 mmol), trans-1,2-bis(methylamino)cyclohexane (15 mg, 0.108 mmol) and K2CO3 (74 mg, 0.542 mmol) were dissolved in 1 mL of dioxane in a screw cap vial and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was stirred at 110° C. for 18 h. The reaction mixture filtered and concentrated, then purified by preparative HPLC to give the title compound (7.1 mg). LCMS: 412.2 m/z (M+H)+; ret. Time: 3.24 min (Analytical Method A).

Aufarbeitung

customcap vial
customa stream of nitrogen was bubbled through the mixture for 2 minutes
filtrationThe reaction mixture filtered
concentrationconcentrated
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-9a888af2c8b642b59563c8d3106b1c25
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541418B2

Verknüpfte Notizen

Wird geladen…