Reacción #1144436

Ecuación de reacción

acetic acid

lithium diisopropylamide

1-butyl-5-ethyluracil

tetrahydrofuran

tetrahydrofuran

diphenyl disulfide

tetrahydrofuran

→

1-butyl-5-ethyl-6-phenylthiouracil

Rendimiento 7.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to −70° C. again
2. 2
   workup.STIRRINGstirred for 20 minutes
3. 3
   Otrobrought to room temperature
4. 4
   Lavadowashed with saturated aqueous solution of sodium chloride
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   Lavadoeluted with 10% ethyl acetate/hexane
7. 7
   Otrocrystallized from hexane

Procedimiento

Then, a solution of 4.4 mmol of lithium diisopropylamide in 2.8 ml of tetrahydrofuran was added dropwise to a solution of 392 mg (2.0 mmol) 1-butyl-5-ethyluracil in 9 ml of tetrahydrofuran under a nitrogen atmosphere at −70° C. and stirred for 70 minutes at −70° C. and further 5 minutes at −25° C. The mixture was cooled to −70° C. again, added with a solution of 567 mg (2.6 mmol) diphenyl disulfide in 3 ml of tetrahydrofuran, stirred for 20 minutes, added with 1 ml of acetic acid, brought to room temperature, washed with saturated aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was adsorbed on a silica gel, eluted with 10% ethyl acetate/hexane and crystallized from hexane to obtain 40 mg of 1-butyl-5-ethyl-6-phenylthiouracil (Yield: 7%).

Fuente