Methanol → 4,6-Diaminonicotinonitrile

HRID 617924Notes

Reaction equation

HRID 617924 reaction equation
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[C:10]#[N:11].[H][H].C([O-])(=O)C.[K+].CO>[Pd].O1CCCC1>[NH2:8][C:6]1[CH:5]=[C:4]([NH2:9])[C:3]([C:10]#[N:11])=[CH:2][N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1706684,6-Diamino-2-bromo-3-pyridinecarbonitrileHCID 517044Potassium AcetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 2958964,6-Diaminonicotinonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 21.3 g of 6-bromo-2,4-diamino-5-cyanopyridine (JACS, 80:2838-2840 (1958)) and 1 g of 20% palladium on charcoal in 250 mL of tetrahydrofuran was shaken in a Parr apparatus under an atmosphere hydrogen. After 2 hours, the reaction was stopped and 10 g of potassium acetate and 50 mL of methanol added. The reaction was recharged with hydrogen and shaken for 18 hours. The solvents were removed under reduced pressure and the residue crystallized from isopropyl alcohol to afford the title compound 2,4-diamino-5-cyanopyridine, mp 201-202° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-c68c356a278b4eea9c94eb125607496a
Source dataset
uspto-grants-1999_09
Patent number
US05952342

Reaction notes

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