4,6-Diamino-2-bromo-3-pyridinecarbonitrile → 4,6-Diaminonicotinonitrile

HRID 1857956Notes

Reaction equation

HRID 1857956 reaction equation
Br[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH2:10])[CH:5]=[C:4]([NH2:11])[N:3]=1.CC([O-])=O.[K+]>O1CCCC1.CO.[Pd]>[C:8]([C:7]1[CH:2]=[N:3][C:4]([NH2:11])=[CH:5][C:6]=1[NH2:10])#[N:9]

Participants

6

Reactant 2

HCID 1706684,6-Diamino-2-bromo-3-pyridinecarbonitrileHCID 517044Potassium Acetate

Product 1

HCID 2958964,6-DiaminonicotinonitrileYield 69.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (II) (15.1 g, 0.071 mol), KOAc (7.0 g, 0.071 mol) and 5% Pd/C (4 g) in THF (tetrahydrofuran) (130 mL) and MeOH (methanol) (70 mL) was hydrogenated (55 psi/20° C.) for 7 days. The resulting solution was filtered over Celite, washing with THF/MeOH, then the solvents were removed under reduced pressure. The residue was dissolved in dilute HCl, then the solution neutralised with 40% NaOH and excess Na2CO3 to give 3-cyano-4,6-diaminopyridine (III) (6.58 g, 69%): mp (water) 197-198° C. [Metzger R., Oberdorfer J., Schwager C., Thielecke W., Boldt P., Liebigs Ann. Chem., 1980;946-953 record mp (benzene) 205° C⟧

Workup

  1. custom(55 psi/20° C.)
  2. customfor 7 days
  3. filtrationThe resulting solution was filtered over Celite
  4. washwashing with THF/MeOH
  5. customthe solvents were removed under reduced pressure
  6. dissolutionThe residue was dissolved in dilute HCl

Sources & evidence

ORD record
ord-47be9b97baed42a99389ba5c44380859
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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