1,4-Dioxane → 5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine

Participants

Reaction Steps

6-Chloro-5-cyano-4-(3-methoxyphenyl)-2-methylthio-pyrimidine (example 1b, 1.46 g) was suspended in 1,4-dioxane (10 ml). Tetrakis(triphenylphosphine)palladium(0) (350 mg) was added and the mixture was flushed with a nitrogen atmosphere. Tetravinyltin (1.26 ml) was added and the mixture was refluxed for 5 h. The reaction mixture was then poured in a mixture of EtOAc (100 ml) and H2O (100 ml). The organic layer was washed with sat. aq. NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/0 to 1/3 (v/v).

Provenance & Evidence