Reaktion #3753

Reaktionsgleichung

1,3-di-n-propyl-5,6-diaminouracil

N-methylmorpholine

1,2,3,4-tetrahydro-2-naphthoic acid

tetrahydrofuran

isobutyl chloroformate

→

1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction for 5 hours at -20° C
2. 2
   TemperaturWarm
3. 3
   Sonstigethe reaction to room temperature
4. 4
   SonstigeSeparate the layers
5. 5
   Waschenrinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml)
6. 6
   Trocknendry over anhydrous magnesium sulfate
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate
9. 9
   SonstigePurify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate)

Vorschrift

Dissolve 1,2,3,4-tetrahydro-2-naphthoic acid (1.0 g, 5.67 mmol) in tetrahydrofuran (40 ml). Add N-methylmorpholine (0.62 ml, 5.67 mmol) and cool to -20° C. Add isobutyl chloroformate (0.73 ml, 5.67 mmol) and stir for 25 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.28 g, 5.67 mmol, in 5 ml dimethylformamide) and stir the reaction for 5 hours at -20° C. Warm the reaction to room temperature and dilute with diethyl ether (300 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml), dry over anhydrous magnesium sulfate, filter and concentrate. Purify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate) to provide 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide (2.0 g) as a foam.

Quelle