Potassium Carbonate → Tert-butyl cyclopropyl(6-ethynyl-3-formylimidazo[1,2-a]pyrazin-8-yl)carbamate

HRID 624763Notes

Reaction equation

HRID 624763 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]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86714609Tert-butyl cyclopropyl(3-formyl-6-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazin-8-yl)carbamate

Product 1

HCID 86714610Tert-butyl cyclopropyl(6-ethynyl-3-formylimidazo[1,2-a]pyrazin-8-yl)carbamateYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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]+.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was partitioned between dichloromethane (10 mL) and water (10 mL)
  3. extractionThe aqueous layer was further extracted with dichloromethane (2×10 mL)
  4. washThe organics were washed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6eb1f3957c6f4322932c09ac3f3374ac
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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