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

HRID 1963953Notes

Reaction equation

HRID 1963953 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.CS(C)=O.[O:13]1[CH2:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15][CH2:14]1>C(OCC)(=O)C>[Cl:8][C:4]1[N:3]=[C:2]([NH:20][CH2:19][CH:16]2[CH2:17][CH2:18][O:13][CH2:14][CH2:15]2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 785042,6-DichloropyrazineHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 534102886-Chloro-N-[(tetrahydro-2H-pyran-4-yl)methyl]-2-pyrazinamineYield 81.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2,6-dichloropyrazine (950 mg, 6.38 mmol), DMSO (14 ml), TEA (1.067 ml, 7.65 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (771 mg, 6.70 mmol) was stirred at 75° C. for 6 hours, and the reaction progress was followed by LCMS. The crude reaction mixture was cooled to ambient temperature, diluted with 300 ml of ethyl acetate, washed with 1M NaOH soln.(1×), water (1×), saturated salt soln. (1×), dried with sodium sulfate, filtered, and concentrated to constant mass, giving 1185 mg of titled compound as free base, used without further purification. LCMS (m/z): 228.0 (MH+), retention time=0.73 min.

Workup

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

Sources & evidence

ORD record
ord-3b291a4634eb4f3ea0b35d8ace3576fc
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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