Reaktion #483454

Reaktionsgleichung

Na2S2O3

1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil

ethanol

iodine crystals

→

title compound

Ausbeute 82.0%

4-[1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]benzaldehyde

Ausbeute 82.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated at reduced pressure
2. 2
   Sonstigeand residual ethanol was removed by evaporation from dimethoxyethane (400 ml)
3. 3
   workup.DISSOLUTIONThe resulting yellow solid was dissolved in dimethoxyethane (1 L)
4. 4
   workup.STIRRINGThe reaction mixture was stirred at 50° C. for 4 h and at room temperature overnight
5. 5
   Sonstigethe dimethoxyethane was removed at reduced pressure
6. 6
   FiltrationThe resulting solid was collected by filtration
7. 7
   TemperaturAfter heating
8. 8
   Temperaturat reflux for ten minutes
9. 9
   Filtrationthe solids were collected by filtration
10. 10
    Sonstigedried

Vorschrift

1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil (143.5 mmol) was freshly prepared as described in Example 1d and dissolved in absolute ethanol (1 L). Terepthaldehyde monodiethylacetal (Aldrich, 28.54 ml, 143.5 mmol) was added and the solution was stirred at room temperature for 3h. The reaction mixture was concentrated at reduced pressure. and residual ethanol was removed by evaporation from dimethoxyethane (400 ml). The resulting yellow solid was dissolved in dimethoxyethane (1 L) and iodine crystals (40.06 g, 157.85 mmol) were added. The reaction mixture was stirred at 50° C. for 4 h and at room temperature overnight. Saturated Na2S2O3 (300 ml) was added and the dimethoxyethane was removed at reduced pressure. The resulting solid was collected by filtration and combined with methanol (300 ml), H2O (100 ml) and conc. Hydrochloric acid (3 ml). After heating at reflux for ten minutes, the solids were collected by filtration and dried to provide the title compound as a tan solid (53.05 g, 82% yield). 1H-NMR (400 MHz, DMSO-d6) δ: 14.13 (s, 1H), 10.05 (s, 1H), 8.31 (d, J=8.2 Hz, 2H), 8.03 (d, J=8.2 Hz, 2H), 3.91 (br d, J=7 Hz, 2H), 3.77 (br d, J=7 Hz, 2H), 1.93 (m, 1H), 1.74 (m, 1H), 1.60 (m, 10H), 1.20-0.90 (m, 10H). MS (ES−): 447 (M−1).

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