Reaktion #3275

Reaktionsgleichung

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

NaH

Methyl chloroacetate

→

[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid methyl ester

Ausbeute 61.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeresulting in a clear solution
2. 2
   Temperaturthe solution was heated at 50° C. for 20 minutes
3. 3
   Temperaturcooled to room temperature
4. 4
   SonstigeThe resulting precipitate was removed by filtration
5. 5
   Waschenwashed with water
6. 6
   ExtraktionThe aqueous filtrate was extracted with ethyl acetate
7. 7
   Trocknenthe organic layer was dried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigepurified by flash chromatography
11. 11
    Wascheneluting with a gradient of 1:1 hexane

Vorschrift

To a suspension of NaH (60% in mineral oil, 38 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (203 mg, 0.66 mmol). The mixture was heated at 50° C. for 40 minutes resulting in a clear solution. Methyl chloroacetate (90 μL, 1.03 mmol) was added, and the solution was heated at 50° C. for 20 minutes, then cooled to room temperature and poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The aqueous filtrate was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate, filtered, and concentrated. The solids were combined and purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to all ethyl acetate to provide 152 mg (61%) of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid methyl ester; mp 188°-190° C.

Quelle