Reaktion #523590

Reaktionsgleichung

phosgene

acetone ammonia

2-(m-fluoroanilino)-3-methylaminomethylpyridine

sodium hydride

carbon tetrachloride phosgene

→

1-(m-fluorophenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine

Ausbeute 50.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturdropwise under ice-cooling
2. 2
   workup.STIRRINGthe resulting mixture was stirred for 1 hour
3. 3
   Sonstigethe solvent was removed from the reaction mixture by distillation under reduced pressure
4. 4
   SonstigeThe residue thus obtained
5. 5
   Extraktionextracted with ether
6. 6
   Wascheneluted with ether
7. 7
   EinengenThe eluate was concentrated
8. 8
   workup.WAITleft

Vorschrift

To a solution of 2.3 g of 2-(m-fluoroanilino)-3-methylaminomethylpyridine was added 0.96 g of approximately 50% sodium hydride and the mixture was stirred at room temperature for 30 minutes. To this was added 10 g of approximately 30% carbon tetrachloride-phosgene solution, dropwise under ice-cooling, and the resulting mixture was stirred for 1 hour. After an excess of the phosgene was decomposed with 10% acetone-ammonia solution, the solvent was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was diluted with water, extracted with ether and dehydrated. The ether solution was applied on a column of alumina and then eluted with ether. The eluate was concentrated and left to give 1.3 g of 1-(m-fluorophenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 189° - 192° C.

Quelle