Réaction #3271

Équation de réaction

2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one

2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

NaH

Ethyl iodide

→

2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one

Rendement 55.4%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Autreresulting in a clear solution
2. 2
   Températurecooled to room temperature
3. 3
   AutreThe resulting precipitate was removed by filtration
4. 4
   Autrepartitioned between ethyl acetate and water
5. 5
   AutreThe organic layer was separated
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   LavageFlash chromatography, eluting with ethyl acetate

Mode opératoire

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (172 mg, 0.56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodide (60 μL, 0.75 mmol) was added, and the solution was stirred at 50° C. for 3.5 hours, cooled to room temperature, and poured into 30 mL of ice water. The resulting precipitate was removed by filtration and partitioned between ethyl acetate and water. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography, eluting with ethyl acetate, provided 104 mg (55%) of 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 207°-209° C.

Source