Morpholine → 5-bromo-3-morpholinopyrazin-2(1H)-one

HRID 594041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594041
Br[C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([Br:8])[N:7]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>>[Br:8][C:6]1[N:7]=[C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:3](=[O:9])[NH:4][CH:5]=1

Komponenten

3

Edukt 2

HCID 8083MorpholineHCID 167408633,5-Dibromopyrazin-2(1H)-one

Produkt 1

HCID 205289515-bromo-3-morpholinopyrazin-2(1H)-oneAusbeute 43 %

Versuchsvorschrift

A solution of 3,5-dibromopyrazin-2(1H)-one (1.0 equiv.) in morpholine (5 equiv.) was heated to 100° C. for 24 h. Cooled to room temperature and filtered off the precipitate. The filtrate was partitioned between water and ethyl acetate. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and heptanes (0-50%). The pure fractions were concentrated to yield 5-bromo-3-morpholinopyrazin-2(1H)-one as a white solid in 43% yield. LCMS m/z (M+H)=259.9, Rt=0.41 min.

Aufarbeitung

  1. filtrationfiltered off the precipitate
  2. customThe filtrate was partitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified via silica gel column chromatography
  7. washeluting with ethyl acetate and heptanes (0-50%)
  8. concentrationThe pure fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-8f2d581c0aa948adb1a052e8cd7633f9
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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