Reaction #1702115

Reaction equation

tert-butyl [3-(aminomethyl)phenyl]carbamate

2,4,5-trichloropyrimidine

potassium carbonate

→

desired product

Yield 92.3%

tert-Butyl(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)carbamate

Yield 92.3%

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
   OtherThe resulted residue was triturated with methylene chloride and hexanes

Procedure

To a solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (0.50 g, 2.2 mmol) and 2,4,5-trichloropyrimidine (0.45 g, 2.5 mmol) in N,N-dimethylformamide (6 mL) was added potassium carbonate (0.62 g, 4.5 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. The resulted residue was triturated with methylene chloride and hexanes to give the desired product as an off-white powder (0.75 g, 90%). LCMS for C12H11Cl2N4O2 (M-tBu+H)+: m/z=313.0, 315.0.

Source