Sodium Hydroxide → (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(4-(methylsulfonyl)phenyl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

HRID 2093698

Reaktionsgleichung

Reaktionsgleichung von HRID 2093698
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.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].[OH-].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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[C:33]4[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=4)[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

6

Edukt 3

HCID 14798Sodium HydroxideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Produkt 1

HCID 58405285(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(4-(methylsulfonyl)phenyl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-oneAusbeute 2,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 0.15 g, 0.37 mmol), 4-(methylsulfonyl)phenylboronic acid (0.148 g, 0.74 mmol), aqueous sodium hydroxide (240 μL of 3N) and Pd(PPh3)4 (42 mg, 0.037 mmol) were dissolved in 1.2 mL of DME/H2O (5/1, v/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was stirred at 90° C. for 18 h. The reaction mixture was diluted with brine, extracted with EtOAc, dried with Na2SO4 then purified by silica gel column chromatography and preparative HPLC to give to give the title compound (3.8 mg). LCMS: 481.2 m/z (M+H)+; ret. Time: 6.19 min (Analytical Method C).

Aufarbeitung

  1. customv/v) and a stream of nitrogen was bubbled through the mixture for 2 minutes
  2. additionThe reaction mixture was diluted with brine
  3. extractionextracted with EtOAc
  4. dry with materialdried with Na2SO4
  5. customthen purified by silica gel column chromatography and preparative HPLC
  6. customto give

Quellen und Nachweise

ORD-Eintrag
ord-2f930364997b41ea91d46fdc88de18fe
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445503B2

Verknüpfte Notizen

Wird geladen…