Reacción #2298626

ord-34e2d7db353e435aa16e02584e3844b6

Ecuación de reacción

O=c1[nH]cnc2cc(-c3ccsc3)sc12
6-(3-thienyl)-3H-thieno[3,2-d]pyrimid-4-one
O=c1[nH]cnc2cc(-c3ccsc3)sc12
6-(3-Thienyl)-3H-thieno[3,2-d]pyrimid-4-one
O=P(Cl)(Cl)Cl
phosphorus oxychloride
O=C([O-])O.[Na+]
sodium bicarbonate
Clc1ncnc2cc(-c3ccsc3)sc12
6-(3-thienyl)-4-chlorothieno[3,2-d]pyrimidine
Rendimiento 81.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaat reflux for 1 hour
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    LavadoThe organic layer was washed with water
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    Otrothe solvent evaporated under reduced pressure

Procedimiento

A solution of 6-(3-thienyl)-3H-thieno[3,2-d]pyrimid-4-one (218, 74 mg, 0.32 mmol) in phosphorus oxychloride (2 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature, poured into a saturated aqueous solution of sodium bicarbonate to neutralize and then extracted with ethyl acetate. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 6-(3-thienyl)-4-chlorothieno[3,2-d]pyrimidine (65 mg, 81% yield) as a yellow solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE039267E1uspto-grants-2006_09