Реакция #70973

Уравнение реакции

6-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

propane-1-thiol

NaH

→

1,3-Dimethyl-2,4-dioxo-6-(propylthio)-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Растворители

1,4-dioxane

1,4-dioxane

Условия реакции

Обработка

1. 1
   Другоеwas consumed (monitored by TLC)
2. 2
   workup.ADDITIONThen the mixture was poured onto ice water (50 ml)
3. 3
   Экстракцияthe aqueous phase was extracted with ethyl acetate (3×30 ml)
4. 4
   ПромывкаThe combined organic phases were washed with water
5. 5
   Сушкаdried over anhydrous MgSO4
6. 6
   ДругоеThe solvent was evaporated in vacuo
7. 7
   Другоеthe crude product was purified by column chromatography with a mixture of n-hexane:ethyl acetate (1:1) as the eluent

Методика

To a stirred solution of propane-1-thiol (2.30 mmol) in dry 1,4-dioxane (4 ml), NaH (2.30 mmol) was added under argon. To the mixture, a solution of 6-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (2 mmol) in dry 1,4-dioxane (8 ml) was added at 5-8° C. in one portion. The mixture was stirred at room temperature until the starting material was consumed (monitored by TLC). Then the mixture was poured onto ice water (50 ml) and the aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phases were washed with water and dried over anhydrous MgSO4. The solvent was evaporated in vacuo and the crude product was purified by column chromatography with a mixture of n-hexane:ethyl acetate (1:1) as the eluent.

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