Sodium Hydroxide → 2,6-Diaminopyridine-3-carbonitrile

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 204748872,6-Diaminopyridine-3-carboxamide

Product 1

HCID 218881622,6-Diaminopyridine-3-carbonitrileYield 74.2%

Conditions

Temperature: 100 °C

Procedure

2,6-Diamino-nicotinamide (520 mg) described in Manufacturing Example 7-1 and phosphorus oxychloride (5.0 g) were stirred for 0.5 hour at 100° C. The reaction solution was added to 0° C. dilute aqueous sodium hydroxide, which was then extracted with ethyl acetate. The organic layer was concentrated and the residue was purified with NH silica gel column chromatography (ethyl acetate) to obtain the titled compound (340 mg).

Workup

extractionwas then extracted with ethyl acetate
concentrationThe organic layer was concentrated
customthe residue was purified with NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-7f886482509f4db68bfcb5fd94c37ebe
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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