Réaction #1763392

Équation de réaction

1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate

5-chloro-4-hydroxypyridin-2(1H)-one

cesium carbonate

→

desired product

5-chloro-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was cooled to rt
2. 2
   Lavagewashed with H2O (3×)
3. 3
   SéchageThe organic layer was dried over Na2SO4
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Autreto give a yellow solid
6. 6
   AutreThe residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Mode opératoire

A mixture of 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate (800 mg, 2.67 mmol), 5-chloro-4-hydroxypyridin-2(1H)-one (389 mg, 2.67 mmol, AK Scientific) and cesium carbonate (2612 mg, 8.02 mmol) in DMF (20 mL) was heated at 120° C. for 6 h. The reaction was cooled to rt, diluted with EtOAc (30 mL), and washed with H2O (3×). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give a yellow solid. The residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) to give the desired product as a yellow solid. MS (ESI) 379 (M+H).

Source