Ethyl (5-bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)carbamate → 5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-amine
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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.