N-bromobutanimide → (5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)methanol

HRID 1772587Notes

Reaction equation

HRID 1772587 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1>C(#N)C>[Br:25][C:10]1[N:9]2[CH:13]=[C:14]([CH2:16][OH:17])[N:15]=[C:8]2[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 117728187(8-Morpholinoimidazo[1,2-a]pyrazin-2-yl)methanol

Product 1

HCID 117727888(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)methanolYield 45.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of compound 1d (2.40 g, 10.3 mmol) in ACN (200 mL) was added NBS (2.40 g, 13.5 mmol) in portions at −20° C. The resulting solution was stirred at −20° C. for 2 h, and was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:1 v/v) to obtain compound 1e as a yellow solid (1.48 g, 41% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C11H13BrN4O2: 313.0 (M+H). Found 313.2.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with EtOAc/petroleum ether (1:1 v/v)

Sources & evidence

ORD record
ord-2d02f32f55504872bc963e8ffeceb846
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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