Acetylpyrazine → (E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-one

HRID 416224

Reaction equation

HRID 416224 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CCN(CC)CC.COC(C)(C)C>[CH3:12][N:13](/[CH:15]=[CH:2]/[C:1]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)=[O:3])[CH3:14]

Participants

5

Reactant 2

HCID 30914AcetylpyrazineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5825354(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-oneYield 81.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of acetylpyrazine (5 g, 40.9 mmol) in N,N-dimethylformamide dimethyl acetal (10.9 mL, 81.8 mmol) and Et3N (5.7 mL) was heated at 110° C. for 16 h. The heating was stopped and a precipitate was formed while it was allowed to cool down to room temperature. The suspension was diluted with tert-butyl methyl ether; the solid was separated by filtration and washed with tert-butyl methyl ether. This material was triturated with the same solvent, filtered off and dried to afford the title compound 23a as a yellow solid (5.9 g, 33.3 mmol, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.09 (s, 1H), 8.73 (d, J=2.4 Hz, 1H), 8.66 (dd, J=2.4, 1.6 Hz, 1H), 7.84 (d, J=12.4 Hz, 1H), 6.30-6.20 (m, 1H), 3.19 (s, 3H), 2.93 (s, 3H).

Workup

  1. customa precipitate was formed while it
  2. customthe solid was separated by filtration
  3. washwashed with tert-butyl methyl ether
  4. customThis material was triturated with the same solvent
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-fc1dd4dd780c44d7b0412d37f347e4b9
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Linked notes

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