Réaction #2298626

ord-34e2d7db353e435aa16e02584e3844b6

Équation de réaction

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
Rendement 81.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureat reflux for 1 hour
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    LavageThe organic layer was washed with water
  4. 4
    Séchagedried over anhydrous magnesium sulfate
  5. 5
    Autrethe solvent evaporated under reduced pressure

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE039267E1uspto-grants-2006_09