Reaction #1702138

Reaction equation

(1S)-1-(3-methoxyphenyl)ethanamine

2,4,5-trichloropyrimidine

potassium carbonate

→

desired product

Yield 96.0%

2,5-Dichloro-N-[(1S)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

Yield 96.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe reaction was quenched with water
2. 2
   workup.ADDITIONThen EtOAc 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
6. 6
   Dryingdried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

To a solution of (1S)-1-(3-methoxyphenyl)ethanamine (1.50 g, 9.92 mol) (S-isomer, >99% ee purity) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.1 g, 30 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. Then 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 then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow thick oil (2.84 g, 96%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0, 300.0, 302.0 (9:6:1).

Source