Reacción #3275

Ecuación de reacción

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

Rendimiento 61.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroresulting in a clear solution
2. 2
   Temperaturathe solution was heated at 50° C. for 20 minutes
3. 3
   Temperaturacooled to room temperature
4. 4
   OtroThe resulting precipitate was removed by filtration
5. 5
   Lavadowashed with water
6. 6
   ExtracciónThe aqueous filtrate was extracted with ethyl acetate
7. 7
   Secadothe organic layer was dried over magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated
10. 10
    Otropurified by flash chromatography
11. 11
    Lavadoeluting with a gradient of 1:1 hexane

Procedimiento

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.

Fuente