Reaction #53329

Reaction equation

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

Yield 19.4%

Conditions

Workup

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

Procedure

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).

Source