Reacción #895

ord-bbaa547034cb4578bce2648d1c091a1f

Ecuación de reacción

C[S-].[Na+]
sodium thiomethoxide
Clc1cc(Cl)nc(OCc2ccccc2)n1
4,6-dichloro-2-(phenylmethoxy)pyrimidine
CSc1cc(Cl)nc(OCc2ccccc2)n1
4-chloro-6-methylthio-2-(phenylmethoxy)pyrimidine

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto react for 2 hours
  2. 2
    Otrothe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  3. 3
    LavadoThe organic layer was washed with aqueous saturated sodium chloride
  4. 4
    Secadodried over anhydrous sodium sulfate
  5. 5
    Concentraciónconcentrated
  6. 6
    Otropurified on a silica gel column

Procedimiento

Aqueous sodium thiomethoxide (15%, 2.75 g, 0.0059×1.0 mol) was added dropwise in 4,6-dichloro-2-(phenylmethoxy)pyrimidine (Compound No. II-26) (1.5 g, 0.0059 mol) dissolved in THF at room temperature. After allowed to react for 2 hours, the reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, then purified on a silica gel column to obtain 4-chloro-6-methylthio-2-(phenylmethoxy)pyrimidine (Compound No. II-15) as an intermediate.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723412uspto-grants-1998_03