Reaction #431027

Reaction equation

1-naphthyl boronic acid

2-amino-4-chloro-5,6-dimethylpyrimidine

ethyl alcohol

sodium carbonate

→

2-amino-5,6-dimethyl-4-(naphth-1-yl)-pyrimidine

Yield 38.5%

Solvents

1,2-dimethoxyethane

water

Conditions

Workup

1. 1
   Temperatureto reflux (about 80° to 90° C.) for 14 hours
2. 2
   Filtrationfiltered
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe solvent was removed under reduced pressure
5. 5
   Otherthe resultant yellow solid was recrystallized

Procedure

A stirred heterogeneous solution of 1-naphthyl boronic acid (0.382 g), 2-amino-4-chloro-5,6-dimethylpyrimidine (0.350 g), tetrakis(triphenylphosphine)palladium(0) (0.153 g), ethyl alcohol (8 mL), water (4 mL), 1,2-dimethoxyethane (8 mL) and sodium carbonate (0.85 g), was heated to reflux (about 80° to 90° C.) for 14 hours. The solution was then cooled to room temperature, filtered and extracted with ethyl acetate. The solvent was removed under reduced pressure and the resultant yellow solid was recrystallized to give 2-amino-5,6-dimethyl-4-(naphth-1-yl)-pyrimidine (0.213 g), m.p. 213.5°-215.1° C.

Source