Reacción #86516

Ecuación de reacción

7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

phenylboronic acid

sodium carbonate

→

desired product

Rendimiento 44.4%

7-(1-azidoethyl)-3-methyl-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Rendimiento 44.4%

Disolventes

1,4-dioxane

water

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to rt
2. 2
   Lavadowashed with water, brine
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was purified on silica gel
6. 6
   Lavadoeluting with 0 to 50% EtOAc in hexane

Procedimiento

To a mixture of 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.100 g, 0.318 mmol) and phenylboronic acid (46.6 mg, 0.382 mmol) in 1,4-dioxane (2 mL) was added a 1 M solution of sodium carbonate (40.5 mg, 0.382 mmol) in water (0.38 mL) and tetrakis(triphenylphosphine)palladium (0) (18.4 mg, 0.0159 mmol). The reaction mixture was heated at 100° C. overnight. After cooling to rt, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexane, to provide the desired product (44 mg, 44.4%). LCMS calculated for C15H14N5OS (M+H)+: m/z=312.1. Found: 312.3.

Fuente