Reacción #53329

Ecuación de reacción

chloroacetic acid methyl ester

sodium hydride

compound ( 1 )

4-[[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

DMF

→

methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycine

Rendimiento 19.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was then quenched with water
2. 2
   Filtraciónthe resulting solid was filtered off
3. 3
   workup.ADDITIONThe residue was treated with hot ACN
4. 4
   Filtraciónfiltered while still hot
5. 5
   OtroThe residue from the cooled filtrate was recrystallized from 1,4-dioxane
6. 6
   FiltraciónThe precipitate was filtered off

Procedimiento

A solution of sodium hydride (0.00195 mol) in DMF (7 ml) was added to compound (1) (0.00186 mol) and the resulting solution was stirred for 5 minutes under argon. Then, chloroacetic acid methyl ester (0.0186 mol) was added and the reaction mixture was heated to 70° C. for 19 hours. The reaction mixture was then quenched with water and the resulting solid was filtered off. The residue was treated with hot ACN, then filtered while still hot. The residue from the cooled filtrate was recrystallized from 1,4-dioxane. The precipitate was filtered off, yielding 0.16 g (19.4%) of methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycine (compound 39).

Fuente