Reaction #63196

Reaction equation

3-[4-(5-bromo-3-methylpyrid-2-yl)butyl]-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]-pyridine

ammonium hydroxide

→

title compound

2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-3-hydroxy-5-(pyrid-3-ylmethyl)pyridine

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Otherto give a solution of ca. pH 8
3. 3
   Extractionextracted with chloroform (4×30 ml)
4. 4
   DryingThe combined chloroform extracts were dried over magnesium sulphate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherthe residue was chromatographed on silica
7. 7
   Washeluted with 7.5% v/v methanol in chloroform
8. 8
   Othercrystallised under ether

Procedure

A mixture of 3-[4-(5-bromo-3-methylpyrid-2-yl)butyl]-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]-pyridine (0.6 g) and polyphosphoric acid (ca. 6 g) was heated with stirring at 190°-200° C. for 40 minutes. The cooled residue was dissolved in aqueous ammonium hydroxide to give a solution of ca. pH 8 and extracted with chloroform (4×30 ml). The combined chloroform extracts were dried over magnesium sulphate, concentrated in vacuo and the residue was chromatographed on silica eluted with 7.5% v/v methanol in chloroform and then crystallised under ether to give the title compound (0.12 g), m.p. 164°-166° C.

Source