Dimethyl Sulfoxide → 6-Chloro-N-methyl-N-(tetrahydro-2H-pyran-4-ylmethyl)-2-pyrazinamine

HRID 1963959Notes

Reaction equation

HRID 1963959 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.CS(C)=O.[CH3:13][NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(OCC)(=O)C>[Cl:8][C:4]1[N:3]=[C:2]([N:14]([CH3:13])[CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 785042,6-DichloropyrazineHCID 22225668Tetrahydro-N-methyl-2H-pyran-4-methanamine

Product 1

HCID 534103026-Chloro-N-methyl-N-(tetrahydro-2H-pyran-4-ylmethyl)-2-pyrazinamineYield 98.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,6-dichloropyrazine (298 mg, 2.000 mmol), DMSO (6 ml), TEA (0.418 ml, 3.00 mmol) and N-methyl-1-(tetrahydro-2H-pyran-4-yl)methanamine (264 mg, 2.040 mmol) was stirred at 70° C. for 16 hours, and the reaction progress was followed by LCMS. The crude reaction mixture was let cool to room temperature, diluted with 150 ml of ethyl acetate, washed with 1M NaOH soln. (1×), water (2×), saturated salt soln. (1×), dried with sodium sulfate, filtered, and concentrated to constant mass, giving 475 mg of the title compound as free base, which was used without further purification. LCMS (m/z): 242.0 (MH+), retention time=0.85 min.

Workup

  1. customThe crude reaction mixture
  2. temperaturewas let cool to room temperature
  3. washwashed with 1M NaOH soln
  4. dry with material(1×), dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to constant mass

Sources & evidence

ORD record
ord-b51dcfce2f5c4c4790c4f782d9c53938
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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