Reaktion #86520

Reaktionsgleichung

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

(3,5-difluorophenyl)boronic acid

sodium carbonate

→

desired product

Ausbeute 38.0%

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

Ausbeute 38.0%

Lösungsmittel

1,4-dioxane

water

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt
2. 2
   Waschenwashed with water, brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue 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, 0.318 mmol) and (3,5-difluorophenyl)boronic acid (60.3 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 40% EtOAc in hexane, to provide the desired product (42 mg, 38.0%). LCMS calculated for C15H12F2N5OS (M+H)+: m/z=348.1. Found: 348.2.

Quelle