Reaction #2328991

Reaction equation

6-Methoxy-1,3-benzoxazole

5-bromo-N,N-dimethylpyrimidin-2-amine

Cs2CO3

→

title compound

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyrimidin-2-amine

Solvents

DMF

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered through celite
2. 2
   Washwashed through with CH2Cl2
3. 3
   Otherthe solvents were removed under reduced pressure
4. 4
   OtherThe crude product was purified by flash chromatography (CH2Cl2/CH2Cl2/MeOH (9:1) gradient)

Procedure

6-Methoxy-1,3-benzoxazole (0.67 mmol), 5-bromo-N,N-dimethylpyrimidin-2-amine (0.80 mmol), CuBr (0.13 mmol), Cs2CO3 (0.67 mmol) and Pd(t-Bu3P)2 (0.067 mmol) in dry DMF (3 ml) was stirred 30 min at 160° C. in a microwave reactor. The reaction mixture was filtered through celite, washed through with CH2Cl2 and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography (CH2Cl2/CH2Cl2/MeOH (9:1) gradient) to give the title compound as an off white solid (108.2 mg). 1H NMR δ ppm 8.99 (s, 2H) 7.62 (d, 1H) 7.38 (d, 1H) 6.98 (dd, 1H) 3.83 (s, 3H) 3.23 (s, 6H); MS m/z 271 (M+H).

Source