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

HRID 1623415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623415
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 534103026-Chloro-N-methyl-N-(tetrahydro-2H-pyran-4-ylmethyl)-2-pyrazinamineAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d65309e6f5754b1f8a9071880b3fd604
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778951B2

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