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

HRID 3193

Reaktionsgleichung

Reaktionsgleichung von HRID 3193
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Komponenten

3

Edukt 2

HCID 6115AnilineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Produkt 1

HCID 53278856-(2,6-dichlorophenyl)-8-methyl-2-(phenylamino)-7H,8H-pyrido[2,3-d]pyrimidin-7-one

Reaktionsbedingungen

Temperatur
184 °C

Versuchsvorschrift

A solution of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 in 1.00 g (10.70 mmol) of aniline was maintained at reflux (184° C.) for 3 minutes. Most of the excess aniline was evaporated at reduced pressure. The remaining gum was dissolved in 1.0 mL of ethyl acetate. Crystals developed on inducement; wt 0.088 g. Further purification to remove dark colors was effected by silica gel chromatography, eluting with chloroform and then 50% hexane-ethyl acetate to obtain pure crystalline product; wt 0.046 g; mp 247°-249° C.

Aufarbeitung

  1. customMost of the excess aniline was evaporated at reduced pressure
  2. dissolutionThe remaining gum was dissolved in 1.0 mL of ethyl acetate
  3. customFurther purification
  4. customto remove dark colors
  5. washeluting with chloroform
  6. custom50% hexane-ethyl acetate to obtain pure crystalline product

Quellen und Nachweise

ORD-Eintrag
ord-0aaab490559345e3a5659881e04302db
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733914

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