Réaction #3329

Équation de réaction

NaH

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

1-Chloro-3-phenylpropane

→

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

Rendement 57.2%

Solvants

dimethylformamide

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autreresulting in a clear solution
2. 2
   Températurethe reaction mixture was heated at 60° C. for 35 minutes
3. 3
   workup.ADDITIONpoured onto ice water
4. 4
   Lavagewashed with water
5. 5
   Séchagedried over magnesium sulfate
6. 6
   FiltrationFiltration
7. 7
   Concentrationfollowed by concentration in vacuo
8. 8
   Autregave an oil that
9. 9
   Autrewas purified by flash chromatography
10. 10
    Lavageeluting with 1:3 hexane
11. 11
    Autreethyl acetate to provide 345 mg of crude product
12. 12
    AutreRecrystallization from ethyl acetate and hexane
13. 13
    Autreby drying in vacuo

Mode opératoire

To a suspension of NaH (60% in mineral oil, 58 mg) in 10 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (320 mg, 1.04 mmol). The mixture was heated to 60° C. resulting in a clear solution. 1-Chloro-3-phenylpropane (260 μL, 1.81 mmol) was added, and the reaction mixture was heated at 60° C. for 35 minutes, then poured onto ice water. The resulting gummy solid was dissolved in ethyl acetate, washed with water, and dried over magnesium sulfate. Filtration, followed by concentration in vacuo, gave an oil that was purified by flash chromatography, eluting with 1:3 hexane:ethyl acetate to provide 345 mg of crude product. Recrystallization from ethyl acetate and hexane followed by drying in vacuo provided 253 mg (57%) of 2-amino-6-(2,6-dichlorophenyl)-8-(3-phenylpropyl)-8H-pyrido[2,3-d]pyrimidin-7-one; mp 161°-163° C.

Source