Reaktion #86539

Reaktionsgleichung

sodium carbonate

water

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

4-fluorophenylboronic acid

→

desired product

Ausbeute 66.0%

7-(1-azidoethyl)-6-(4-fluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Ausbeute 66.0%

Lösungsmittel

1,4-dioxane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Waschenwashed with water, brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe crude mixture was purified on silica gel
6. 6
   Wascheneluting with 0 to 40% EtOAc in hexane

Vorschrift

To a mixture of 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.10 g, 0.32 mmol) and 4-fluorophenylboronic acid (53 mg, 0.38 mmol) in 1,4-dioxane (2 mL) was added a 1 M solution of sodium carbonate in water (0.38 mL, 0.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.016 mmol). The reaction mixture was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water, brine, dried over MgSO4, and concentrated. The crude mixture was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired product (69 mg, 66%). LCMS calculated for C15H13FN5OS (M+H)+: m/z=330.1. Found: 330.0.

Quelle