Reacción #3278

Ecuación de reacción

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

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

monomethylamine

→

pure product

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

Disolventes

Dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe tube was cooled in a dry ice-acetone bath
2. 2
   Otrocondensed in the tube
3. 3
   Otrothe tube was closed
4. 4
   Temperaturathe reaction mixture was heated behind a shield in a 110° C. oil bath
5. 5
   TemperaturaThe solution was heated in the oil bath for 20 hours
6. 6
   TemperaturaThe tube was cooled in an ice-acetone bath
7. 7
   Temperaturawarmed to room temperature
8. 8
   OtroMost of the dimethylformamide was evaporated at reduced pressure
9. 9
   Otroto yield crystals
10. 10
    OtroThe solid was triturated with 5 mL of water
11. 11
    Filtraciónfiltered
12. 12
    Lavadowashed with water
13. 13
    Otrodried
14. 14
    OtroPurification
15. 15
    Otrowas effected by recrystallization from ethyl acetate-petroleum ether

Procedimiento

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.

Fuente