تفاعل #3753

معادلة التفاعل

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

المذيبات

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction for 5 hours at -20° C
2. 2
   درجة الحرارةWarm
3. 3
   أخرىthe reaction to room temperature
4. 4
   أخرىSeparate the layers
5. 5
   غسيلrinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml)
6. 6
   تجفيفdry over anhydrous magnesium sulfate
7. 7
   ترشيحfilter
8. 8
   تركيزconcentrate
9. 9
   أخرىPurify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate)

الإجراء التجريبي

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.

المصدر