Reaktion #2030994

Reaktionsgleichung

morpholine

hexyl iodide

8-chloro-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

sodium carbonate

→

title compound

Ausbeute 54.4%

8-chloro-3-hexyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione

Ausbeute 54.4%

Lösungsmittel

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe reaction vessel evacuated
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGstirring at room temperature under nitrogen
5. 5
   workup.WAITcontinued for 4 hours
6. 6
   Waschenwashed with 2M HCl aq. (25 ml)
7. 7
   ExtraktionThe organic extract
8. 8
   Trocknenwas dried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigePurification by aminopropyl SPE (5 g)
12. 12
    Waschenwashing with MeOH
13. 13
    Waschenbefore eluting the product with 5% AcOH/MeOH

Vorschrift

To a solution of 8-chloro-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.42 mmol) in anhydrous DMF (3 ml) was added sodium carbonate (58 mg, 0.54 mmol), after 10 minutes stirring hexyl iodide (0.08 ml, 0.54 mmol) was added and the reaction mixture stirred at room temperature under nitrogen for 90 hours. Pd(PPh3)4 (73 mg, 0.063 mmol) was then added and the reaction vessel evacuated and flushed with nitrogen (×3), morpholine (0.37 ml, 4.3 mmol) was added and stirring at room temperature under nitrogen continued for 4 hours. The reaction mixture was diluted with EtOAc (25 ml) and washed with 2M HCl aq. (25 ml). The organic extract was dried (MgSO4) filtered and evaporated. Purification by aminopropyl SPE (5 g) loading the compound and washing with MeOH before eluting the product with 5% AcOH/MeOH afforded the title compound as a white solid (65 mg, 54%). NMR; δH (400 MHz, d6-DMSO)) 0.85 (t, 3H, J=7 Hz), 1.23-1.33 (m, 6H), 1.58-1.68 (m, 2H), 3.22 (s, 3H), 3.91 (t, 2H, J=7.5 Hz), 14.46 (br. s, 1H); m/z 285.3 [MH+].

Quelle