Reaktion #3309

Reaktionsgleichung

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

6-(2,6-Dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

4-aminophenylacetic acid, methyl ester

acetic acid

→

{4-[6-(2,6-Dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]phenyl}-acetic acid, methyl ester

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated in a 160° C. to 165° C. oil bath
2. 2
   TemperaturThe resulting solution was heated for 10 minutes
3. 3
   workup.DISSOLUTIONto dissolve
4. 4
   Sonstigeto precipitate a gum
5. 5
   SonstigeThe mixture was decanted
6. 6
   workup.DISSOLUTIONthe remaining gum was dissolved in 20 mL of chloroform
7. 7
   WaschenThe chloroform solution was washed with 25 mL of water
8. 8
   Trocknendried (magnesium sulfate)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigePurification
12. 12
    Wascheneluting with chloroform
13. 13
    Sonstigewith 50% hexane/ethyl acetate to obtain the fraction
14. 14
    workup.ADDITIONcontaining pure product
15. 15
    EinengenThe eluent was concentrated to dryness
16. 16
    Sonstigeto obtain a solid

Vorschrift

A mixture of 0.226 g (0.58 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.40 g (2.80 mmol) of 4-aminophenylacetic acid, methyl ester base was heated in a 160° C. to 165° C. oil bath. The resulting solution was heated for 10 minutes and cooled to room temperature. The solution was treated with 1 mL of glacial acetic acid to dissolve. Water (10 mL) was added to precipitate a gum. The mixture was decanted, and the remaining gum was dissolved in 20 mL of chloroform. The chloroform solution was washed with 25 mL of water, dried (magnesium sulfate), filtered, and concentrated. Purification was effected by silica gel chromatography eluting with chloroform and then with 50% hexane/ethyl acetate to obtain the fraction containing pure product. The eluent was concentrated to dryness to obtain a solid; wt 0.141 g.

Quelle