Potassium Carbonate → Tert-butyl cyclopropyl(6-ethynyl-3-formylimidazo[1,2-a]pyrazin-8-yl)carbamate
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([N:10]([C:18]2[C:19]3[N:20]([C:30]([CH:33]=[O:34])=[CH:31][N:32]=3)[CH:21]=[C:22]([C:24]#[C:25][Si](C)(C)C)[N:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH2:8]1>CO>[CH:7]1([N:10]([C:18]2[C:19]3[N:20]([C:30]([CH:33]=[O:34])=[CH:31][N:32]=3)[CH:21]=[C:22]([C:24]#[CH:25])[N:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium carbonate (86 mg, 0.63 mmol) was added to tert-butyl cyclopropyl(3-formyl-6-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazin-8-yl)carbamate (50 mg, 0.13 mmol) dissolved in methanol (2.5 mL). After 2 h, the volatiles were removed in vacuo. The residue was partitioned between dichloromethane (10 mL) and water (10 mL). The aqueous layer was further extracted with dichloromethane (2×10 mL). The organics were washed with brine (30 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (30% EtOAc/hexanes) to provide tert-butyl cyclopropyl(6-ethynyl-3-formylimidazo[1,2-a]pyrazin-8-yl)carbamate (20 mg, 50%) as a yellow foamy solid. LCMS (ES): >95% pure, m/z 327 [M+1]+.