Reaction #3753

Reaction equation

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

Solvents

diethyl ether

Conditions

Workup

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

Procedure

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