Cyanuric acid → 2-Methylpyridine-3-carbonitrile

HRID 1919839Notes

Reaction equation

HRID 1919839 reaction equation
N1C(=O)NC(=O)NC1=O.[CH3:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=O>CN(C=O)C>[CH3:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]#[N:15]

Participants

4

Reactant 2

HCID 7956Cyanuric acidHCID 122437052-Methylnicotinamide2×

Product 1

HCID 47383082-Methylpyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanuric acid (418 mg, 2.2 mmol) was added in one portion to a suspension of 2-methyl-nicotinamide (intermediate 29) (613 mg, 4.5 mmol) in 2.5 ml of DMF cooled in ice. The reaction was stirred for 2.5 hours then poured into ice. The reaction was extracted with ethyl acetate until the organic layer no longer contained product. The combined organic layers, were dried over Na2SO4, filtered and concentrated. Purified on normal phase chromatography with ethyl acetate/heptane 0 to 50 gradient then 50/50 EA/heptane. Yield (216 mg, 41%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.78 (s, 3 H), 7.25 (dd, J=7.71, 4.98 Hz, 1 H), 7.89 (dd, J=7.81, 1.56 Hz, 1 H), 8.68 (s, 1 H)

Workup

  1. temperaturecooled in ice
  2. additionthen poured into ice
  3. extractionThe reaction was extracted with ethyl acetate until the organic layer no longer contained product
  4. dry with materialThe combined organic layers, were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified on normal phase chromatography with ethyl acetate/heptane 0 to 50 gradient
  8. customYield (216 mg, 41%)

Sources & evidence

ORD record
ord-348dbcdb5e85489ea6afaffa8cec3381
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

Loading…