Reaktion #51909

Reaktionsgleichung

water

N-(4-fluorobenzyl)-7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxamide

potassium carbonate

iodomethane

→

title compound

Ausbeute 95.0%

N-(4-fluorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Ausbeute 95.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter another 15 minutes the mixture became
2. 2
   workup.STIRRINGa thick slurry that stopped stirring
3. 3
   workup.STIRRINGthe thick slurry was stirred at room temperature over night
4. 4
   Filtrationthe solids were collected by vacuum filtration
5. 5
   Sonstigedried in a vacuum oven at 60° C.

Vorschrift

To a slurry of 3.34 g (9.64 mmol) N-(4-fluorobenzyl)-7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxamide and 1.99 g (14.4 mmol) potassium carbonate in 50 mL anhydrous DMF, was added 0.89 mL (14.3 mmol) iodomethane. The mixture was stirred at room temperature. After 40 minutes the slurry became homogeneous and then cloudy. After another 15 minutes the mixture became a thick slurry that stopped stirring. An additional 30 mL of anhydrous DMF was added and the thick slurry was stirred at room temperature over night. Then, 150 mL of water was added to the slurry and the solids were collected by vacuum filtration and dried in a vacuum oven at 60° C. to provide 3.30 g of title compound as a tan solid.

Quelle