Triethylamine → HCID 66606827, compound

HRID 1028271Notes

Reaction equation

HRID 1028271 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:23]([CH3:26])([CH3:25])[CH3:24])(=O)=O>C1(C)C=CC=CC=1>[CH3:24][Si:23]([N:1]([Si:23]([CH3:26])([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 66606827HCID 66606827, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

About 6.17 g of 5-amino-2-pyridinecarbonitrile, 11.54 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 25.34 g of trimethylsilyl trifluoromethanesulfonate in 70 ml of toluene. The resulting mixture was heated to reflux for 2.5 hours and then evaporated under vacuum. The residue was extracted with 100 ml of hexane. The hexane layer was washed twice with saturated aqueous sodium bicarbonate solution (80 ml each time), dried with anhydrous sodium sulfate, and evaporated under vacuum, yielding 5-[bis(trimethylsilyl)amino]-2-pyridinecarbonitrile (BTMSAPyCN) as a green oil (8.67 g, 64% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 8.07 (doublet of doublets, 1H, aromatic proton), 6.70 (doublet of doublets, 1H, aromatic proton), 6.45 (doublet of doublets, 1H, aromatic proton), −0.16 (singlet, 18H, Si—CH3 protons). From the 1H NMR data, the structure of the product was determined to be as follows:

Workup

  1. temperaturecooled with an ice bath
  2. additionTo this mixture was added, in a dropwise fashion
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux for 2.5 hours
  5. customevaporated under vacuum
  6. extractionThe residue was extracted with 100 ml of hexane
  7. washThe hexane layer was washed twice with saturated aqueous sodium bicarbonate solution (80 ml each time)
  8. dry with materialdried with anhydrous sodium sulfate
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-eee94638a443431f8109830fd31acf30
Source dataset
uspto-grants-2014_05
Patent number
US08735494B2

Reaction notes

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