Réaction #3753

Équation de réaction

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

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autrethe reaction for 5 hours at -20° C
2. 2
   TempératureWarm
3. 3
   Autrethe reaction to room temperature
4. 4
   AutreSeparate the layers
5. 5
   Lavagerinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml)
6. 6
   Séchagedry over anhydrous magnesium sulfate
7. 7
   Filtrationfilter
8. 8
   Concentrationconcentrate
9. 9
   AutrePurify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate)

Mode opératoire

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.

Source