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

HRID 3182

Reaktionsgleichung

Reaktionsgleichung von HRID 3182
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:23][NH2:24]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([NH:24][CH3:23])[N:15]=[CH:16][C:11]=2[CH:10]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 53278686-(2,6-Dichlorophenyl)-8-methyl-2-methylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A quantity of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 was placed in a pressure tube with a magnetic stirring bar. The tube was cooled in a dry ice-acetone bath and ca. 3 mL of monomethylamine gas was condensed in the tube. Dimethylformamide (1.0 mL) was added, and the tube was closed and allowed to warm to room temperature. With stirring, the reaction mixture was heated behind a shield in a 110° C. oil bath. After 10 minutes, all solid was in solution. The solution was heated in the oil bath for 20 hours. The tube was cooled in an ice-acetone bath, opened, and warmed to room temperature to vent the excess amine. Most of the dimethylformamide was evaporated at reduced pressure to yield crystals. The solid was triturated with 5 mL of water, filtered, washed with water and dried; wt 0.128 g. Purification was effected by recrystallization from ethyl acetate-petroleum ether to give 0.081 g of pure product; mp 243°-244° C.

Aufarbeitung

  1. temperatureThe tube was cooled in a dry ice-acetone bath
  2. customcondensed in the tube
  3. customthe tube was closed
  4. temperaturethe reaction mixture was heated behind a shield in a 110° C. oil bath
  5. temperatureThe solution was heated in the oil bath for 20 hours
  6. temperatureThe tube was cooled in an ice-acetone bath
  7. temperaturewarmed to room temperature
  8. customMost of the dimethylformamide was evaporated at reduced pressure
  9. customto yield crystals
  10. customThe solid was triturated with 5 mL of water
  11. filtrationfiltered
  12. washwashed with water
  13. customdried
  14. customPurification
  15. customwas effected by recrystallization from ethyl acetate-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a1fc3fad89df44fb9dcbd57241fd99a3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733914

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