反应 #70973

反应方程式

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

溶剂

1,4-dioxane

1,4-dioxane

反应条件

后处理

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

实验过程

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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