Reacción #1144432

Ecuación de reacción

acetic acid

lithium diisopropylamide

1-ethoxymethyl-5-ethyluracil

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

diphenyl disulfide

tetrahydrofuran

→

1-ethoxymethyl-5-ethyl-6-phenylthiouracil

Rendimiento 32.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise over 15 minute
2. 2
   Otroto react for 30 minutes
3. 3
   Otrobrought to room temperature
4. 4
   LavadoThe mixture was washed with water (3 mix 5) and saturated aqueous solution of sodium hydrogencarbonate (twice),
5. 5
   Otrodried on magnesium sulfate
6. 6
   Concentración′ concentrated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17)
8. 8
   Otrocrystallized from ethyl acetate

Procedimiento

Then, 2.2 ml of lithium diisopropylamide (4.4 mmol) solution in tetrahydrofuran (2.1M) was added to 6 ml of tetrahydrofuran under a nitrogen atmosphere at −70° C., to which a solution of 0.40 g (2.0 mmol) of 1-ethoxymethyl-5-ethyluracil in 3 ml of tetrahydrofuran was added dropwise over 15 minute. After stirring for 1 hour at −70° C., the reaction mixture was added with a solution of 0.57 g of diphenyl disulfide in 2 ml of tetrahydrofuran dropwise over 10 minutes and allowed to react for 30 minutes. The reaction mixture was added with 1 ml of acetic acid, brought to room temperature and then added with 30 ml of ethyl acetate. The mixture was washed with water (3 mix 5) and saturated aqueous solution of sodium hydrogencarbonate (twice), dried on magnesium sulfate and′ concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17) and crystallized from ethyl acetate to obtain 0.61 g of 1-ethoxymethyl-5-ethyl-6-phenylthiouracil (Yield: 32%).

Fuente