Methanol → 4,6-Diaminonicotinonitrile

HRID 3415

Reaction equation

HRID 3415 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-07e13572c7374292938c79bf24b4e98d
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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