Reaction #487543

Reaction equation

2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine

methyl 4-amino-2-(3-chloropropoxy)benzoate

→

methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

Solvents

THF

DCM

water

Conditions

Workup

1. 1
   OtherThe organic layer was collected
2. 2
   Dryingdried over sodium sulfate
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherThe crude product was purified by silica gel chromatography
5. 5
   OtherThe product fractions were collected
6. 6
   Concentrationconcentrated under vacuum

Procedure

To a solution of 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine (770 mg, 2.79 mmol) in THF (10 mL) was added methyl 4-amino-2-(3-chloropropoxy)benzoate (681 mg, 2.79 mmol) and Hunig'sBase (1.464 mL, 8.38 mmol). The resulting mixture was stirred for 16 h. The reaction was diluted with DCM and water. The organic layer was collected and dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by silica gel chromatography using 20-40% EtOAc/Hexanes. The product fractions were collected and concentrated under vacuum to give methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate as a solid.

Source