Реакция #3753

Уравнение реакции

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

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Другоеthe reaction for 5 hours at -20° C
2. 2
   ТемператураWarm
3. 3
   Другоеthe reaction to room temperature
4. 4
   ДругоеSeparate the layers
5. 5
   Промывкаrinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml)
6. 6
   Сушкаdry over anhydrous magnesium sulfate
7. 7
   Фильтрацияfilter
8. 8
   Концентрированиеconcentrate
9. 9
   ДругоеPurify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate)

Методика

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.

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