5-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → 5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid

HRID 2105635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105635
C([O:3][C:4]([C:6]12[CH2:13][C:10]([C:14](=O)[NH:15][C:16]3[C:17](=[O:30])[N:18]([CH2:27][CH2:28][CH3:29])[C:19](=[O:26])[N:20]([CH2:23][CH2:24][CH3:25])[C:21]=3[NH2:22])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])C>[OH-].[Na+].CO>[O:26]=[C:19]1[N:20]([CH2:23][CH2:24][CH3:25])[C:21]2[N:22]=[C:14]([C:10]34[CH2:13][C:6]([C:4]([OH:3])=[O:5])([CH2:12][CH2:11]3)[CH2:7][CH2:8][CH2:9]4)[NH:15][C:16]=2[C:17](=[O:30])[N:18]1[CH2:27][CH2:28][CH3:29]

Komponenten

4

Edukt 1

HCID 670783425-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

Produkt 1

HCID 98432695-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acidAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 5-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (0.238 mmol, 0.10 g) in 20% NaOH (2.0 ml) and MeOH (10.0 ml) was stirred and refluxed 5 h. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine, and dried (MgSO4). Filtration and evaporation followed by reverse phase HPLC provided product (0.039 g, 42%) as a solid.

Aufarbeitung

  1. temperaturerefluxed 5 h
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-4b9fc821cad549c4b9338fd4a4d8d7fb
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579354B2

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