Reaction #48373

Reaction equation

HCl

3-azido-5-fluoropyridin-2-amine

Carbonate

→

title compound

Yield 92.8%

5-Fluoropyridine-2,3-diamine

Yield 92.8%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Filtrationthe mixture was filtered
2. 2
   Washrinsed with more tetrahydrofuran
3. 3
   Concentrationconcentrated
4. 4
   workup.DISSOLUTIONThis residue was dissolved in ethanol (50 mL)
5. 5
   Otherpurged with argon, and 10% palladium on carbon
6. 6
   workup.ADDITIONwas added (0.15 g)
7. 7
   workup.ADDITIONHydrogen was introduced (1 atm)
8. 8
   FiltrationThe catalyst was filtered
9. 9
   Otherthe solvent evaporated from the filtrate

Procedure

The HCl salt of 3-azido-5-fluoropyridin-2-amine (1.90 g, 10.0 mmol) was dissolved in tetrahydrofuran (100 mL) and treated with MP-Carbonate (Argonaut, 11.5 g). After 1 h, the mixture was filtered, rinsed with more tetrahydrofuran, and concentrated. This residue was dissolved in ethanol (50 mL), purged with argon, and 10% palladium on carbon was added (0.15 g). Hydrogen was introduced (1 atm) and the reaction stirred until complete. The catalyst was filtered and the solvent evaporated from the filtrate to give the title compound (1.18 g). MS 128.0 (M+1)

Source