Ethyl (5-bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)carbamate → 5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-amine

HRID 1772635Notes

Reaction equation

HRID 1772635 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([NH:11]C(=O)OCC)[N:10]=[C:6]2[C:5]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:4][CH:3]=1>[OH-].[Na+].O>[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([NH2:11])[N:10]=[C:6]2[C:5]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 131734673Ethyl (5-bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)carbamate

Product 1

HCID 1177280545-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of ethyl (5-bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)carbamate (1.2 g, as prepared above) in 5 N aqueous NaOH was heated at reflux for 18 h. The reaction mixture was allowed to cool to rt, diluted with water (50 mL) and extracted with DCM (3×50 mL). The combined DCM layers were dried over Na2SO4 and concentrated under reduced pressure to give compound 21b, which was dried under reduced pressure overnight and used in next step without further purification. Mass Spectrum (LCMS, ESI pos.) Calcd. For C10H12BrN5O: 298.0 (M+H). Found 298.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialThe combined DCM layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4173e56ccfe8429fa5cf93d92bcd8799
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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