Reaction #1702134

Reaction equation

3-(3-methoxyphenyl)propan-1-amine hydrochloride

2,4,5-trichloropyrimidine

potassium carbonate

→

desired product

Yield 91.1%

2,5-Dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine

Yield 91.1%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe reaction was quenched with water
2. 2
   workup.ADDITIONEtOAc was added
3. 3
   Otherthe layers were separated
4. 4
   ExtractionThe aqueous layer was extracted with EtOAc twice
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
   Otherthen triturated with cold EtOAc)

Procedure

To a solution of 3-(3-methoxyphenyl)propan-1-amine hydrochloride (2.00 g, 9.92 mmol) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.80 g, 34.7 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a light brown gel (2.82 g, 91%). LCMS for C14H16Cl2N3O (M+H)+: m/z=312.0, 314.0.

Source