Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204823Generated: November 1, 2026

Sodium Carbonate → tert-butyl N-(5-bromo-3-ethynylpyrazin-2-yl)-N-[(tert-butoxy)carbonyl]carbamate

https://huagongshe.com/reaction/2204823

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantTert-butyl N-tert-butoxycarbonyl-N-[5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl]carbamateHCID 58070279—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Producttert-butyl N-(5-bromo-3-ethynylpyrazin-2-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 5807039494.1%

Reaction Conditions

Temperature90 °C

Reaction Steps

Sodium carbonate (918.5 μL of 2 M, 1.837 mmol) was added to a solution of tert-butyl N-[5-bromo-3-(2-trimethylsilylethynyl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (720 mg, 1.531 mmol) in DMF (2 mL) and the resulting solution heated at 90° C. for 20 minutes. The reaction mixture was allowed to cool to RT and diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organics washed with water, dried (MgSO4) and concentrated in vacuo to give the product as a yellow solid (574 mg, 94% Yield). 1H NMR (400.0 MHz, DMSO) d 1.43 (18H, s), 3.53 (1H, s), 8.55 (1H, s); MS (ES+) 400.03

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365557B2
Source datasetuspto-grants-2016_06
ORD IDord-9395141312ee42d8aee4c5126b9c09c7
Source noteuspto-grants-2016_06