Reaction #955931

Reaction equation

2-(bromomethyl)pyridine hydrobromide

5-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-amine

K2CO3

→

5-(2,4-Dimethylphenyl)-N-(pyridin-2-ylmethyl)-1,3,4-oxadiazol-2-amine

Yield 97.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe solid was dissolved in EtOAc
3. 3
   Washwashed successively with aq. NaHCO3 and brine
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified on silica gel

Procedure

To a solution of 5-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-amine (Example 16a) (94.5 mg, 0.5 mmol) in 5 ml of dry acetonitrile was added K2CO3 (207 mg, 1.5 mmol). To the suspension was added 2-(bromomethyl)pyridine hydrobromide (127 mg, 0.5 mmol) and the mixture was stirred at 90° C. overnight. The solvent was removed under vacuum and the solid was dissolved in EtOAc, washed successively with aq. NaHCO3 and brine, dried over MgSO4 filtered and evaporated. The residue was purified on silica gel to give 5-(2,4-Dimethylphenyl)-N-(pyridin-2-ylmethyl)-1,3,4-oxadiazol-2-amine (136 mg, 97%) as a white solid. 1H NMR (300 MHz, CdCl3): δ 2.34 (s, 3H), 2.5 (s, 3H), 5.1 (s, 2H), 7.07-7.08 (m, 2H), 7.21-7.33 (m, 2H), 7.64-7.68 (m, 2H), 8.59-8.60 (d, 1H); MS (M+H, 281).

Source