Reaction #2328986

Reaction equation

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

hydrogen bromide

sodium bicarbonate

→

title compound

Yield 19.6%

2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-6-ol

Yield 19.6%

Conditions

Workup

1. 1
   Otherthe solid was collected
2. 2
   workup.DISSOLUTIONThe solid was then dissolved in CH2Cl2/ethyl acetate
3. 3
   Dryingdried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated in vacuo

Procedure

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (31 mg, 0.12 mmol) was mixed with hydrogen bromide (48% aq., 2 mL) and a crystal of tetrabutylammonium bromide was added. The reaction was run at 120° C. for 5 minutes in a microwave reactor. The reaction mixture was added to sodium bicarbonate (sat. aq.) and the solid was collected. The solid was then dissolved in CH2Cl2/ethyl acetate, dried (MgSO4), filtered and evaporated in vacuo, giving the title compound (6 mg) as a purple solid. 1H NMR (400 MHz, CD3OD) δ ppm 8.83 (d, 1H) 8.17 (dd, 1H) 7.44 (d, 1H) 7.02 (d, 1H) 6.75-6.88 (m, 2H) 3.19 (s, 6H); MS m/z (M+H) 256; (M−H) 254.

Source