Reaction #1702109

Reaction equation

3-methoxybenzylamine

2,4,5-trichloropyrimidine

potassium carbonate

→

desired product

Yield 93.2%

2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

Yield 93.2%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe reaction was quenched with water
2. 2
   workup.ADDITIONEthyl acetate (“EtOAc”) was added
3. 3
   Otherthe layers were separated
4. 4
   ExtractionThe aqueous layer was extracted with EtOAc once
5. 5
   WashThe combined organic layers were washed with water and brine successively
6. 6
   Dryingdried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   OtherThe crude product was purified by silica gel column chromatography

Procedure

To a solution of 3-methoxybenzylamine (0.75 g, 5.4 mmol) and 2,4,5-trichloropyrimidine (1.1 g, 6.0 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (2.3 g, 16 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with water. Ethyl acetate (“EtOAc”) was added and the layers were separated. The aqueous layer was extracted with EtOAc once. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (1.43 g, 92%). LCMS for C12H12ClN3O (M+H)+: m/z=284.0, 286.0.

Source