Reacción #86522

Ecuación de reacción

2-(tributylstannyl)pyridine

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

→

desired product

Rendimiento 13.1%

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

Rendimiento 13.1%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter being cooled
2. 2
   Otroquenched with saturated ammonium chloride
3. 3
   Extracciónthe resulting mixture was extracted with EtOAc
4. 4
   Lavadowashed with brine
5. 5
   Otrodried
6. 6
   Otroevaporated to dryness
7. 7
   OtroThe residue was purified on silica gel
8. 8
   Lavadoeluting with 0 to 100% EtOAc in hexane

Procedimiento

A mixture of 2-(tributylstannyl)pyridine (Aldrich, 0.176 g, 0.382 mmol), 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (from example 8, step 3; 0.10 g, 0.318 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.0184 g, 0.0159 mmol) in 1,4-dioxane (0.5 mL) was heated at 65° C. overnight. After being cooled and quenched with saturated ammonium chloride, the resulting mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexane, to provide the desired product (13 mg, 13%). LCMS calculated for C14H13N6OS (M+H)+: m/z=313.1. Found: 313.0.

Fuente