Reaktion #86522

Reaktionsgleichung

2-(tributylstannyl)pyridine

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

→

desired product

Ausbeute 13.1%

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

Ausbeute 13.1%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter being cooled
2. 2
   Sonstigequenched with saturated ammonium chloride
3. 3
   Extraktionthe resulting mixture was extracted with EtOAc
4. 4
   Waschenwashed with brine
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe residue was purified on silica gel
8. 8
   Wascheneluting with 0 to 100% EtOAc in hexane

Vorschrift

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.

Quelle