Reacción #3264

Ecuación de reacción

methylamine

4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester

triethylamine

→

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester

Rendimiento 81.0%

Disolventes

hexane

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthen concentrated in vacuo
2. 2
   Otropartitioned between chloroform and saturated aqueous sodium bicarbonate
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   Otroto provide a white solid
8. 8
   Filtraciónfiltered

Procedimiento

To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40% aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91°-93° C.

Fuente