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

HRID 594041Notes

Reaction equation

HRID 594041 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8f2d581c0aa948adb1a052e8cd7633f9
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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