8-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide → 8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 395890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395890
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17]([CH:19]1[CH2:25][CH:24]2[O:26][CH:21]([CH:22]=[CH:23]2)[CH2:20]1)=O>[OH-].[Na+].CO>[CH:21]12[O:26][CH:24]([CH:23]=[CH:22]1)[CH2:25][CH:19]([C:17]1[NH:16][C:3]3[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=3[N:1]=1)[CH2:20]2

Komponenten

4

Edukt 1

HCID 865903668-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

Produkt 1

HCID 102911968-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 8-oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.185 mmol, 0.067 g) in 20% NaOH (1.23 ml) and MeOH (6.2 ml) was stirred and refluxed overnight. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous residue was extracted with Et2O and these extracts discarded. 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 flash column chromatography, eluting with 1:1 EtOAc/CH2Cl2, provided the title compound (0.037 g, 58%) as a beige solid. 1H NMR (300 MHz, CDCl3): 0.93-0.99 (m, 6H), 1.62-1.83 (m, 6H), 2.14-2.25 (m, 2H), 3.40-3.51 (m, 1H), 4.05-1.10 (m, 4H), 4.86 (br s, 2H), 6.25 (s, 2H).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionThe aqueous residue was extracted with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation
  9. washeluting with 1:1 EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b2d8ec3403824642b5ffb25fea4b2fab
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605600B1

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