Reaktion #81911

Reaktionsgleichung

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 iodine

→

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

Ausbeute 55.4%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeresulting in a clear solution
2. 2
   Temperaturcooled to room temperature
3. 3
   SonstigeThe resulting precipitate was removed by filtration
4. 4
   Sonstigepartitioned between ethyl acetate and water
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   WaschenFlash chromatography, eluting with ethyl acetate

Vorschrift

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, .56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodine (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.

Quelle