Dimethylamine → 6-Chloro-N,N-dimethylpyrazine-2-carboxamide

HRID 1693741Notes

Reaction equation

HRID 1693741 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[N:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[CH3:18][N+:19](C)=[C:20](N(C)C)ON1C2N=CC=CC=2N=N1.CNC.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.ClCCl.C1COCC1.C(OCC)(=O)C>[CH3:18][N:19]([CH3:20])[C:8]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[N:7]=1)=[O:10]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145008756-Chloropyrazine-2-carboxylic acid

Product 1

HCID 280647856-Chloro-N,N-dimethylpyrazine-2-carboxamideYield 59.3%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.000 g (6.31 mmol) of 6-chloro-pyrazine-2-carboxylic acid were dissolved in 75 mL of 50% v/v acetonitrile in dichloromethane containing. 2.810 g (7.48 mmol) of N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate were added, then 8.0 mL (16 mmol) of 2 M dimethylamine in anhydrous THF was added and stirring was continued for 18 h. The resulting solution was distributed between ethyl acetate and a 2 M aqueous solution of sodium carbonate. The organic phase was washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes to afford 695 mg (3.74 mmol, 59%) of 6-chloro-pyrazine-2-carboxylic acid dimethylamide as a pale yellow oil. 1H-NMR [500 MHz, d6-DMSO] δ: 8.91 (s, 1H), 8.84 (s, 1H), 3.04 (s, 3H), 2.98 (s, 3H); MS [MH+] m/z: 186.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-72aa3591fc9f4e84b167382f4b003da3
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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