HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2389016Generated: October 30, 2026
Triethylamine → 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine
https://huagongshe.com/reaction/2389016
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 2-Amino-3,5-dibromopyrazine | HCID 620004 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine | HCID 53393189 | 71.8% |
Reaction Steps
To a solution of 3,5-Dibromo-pyrazin-2-ylamine (3.00 g, 11.86 mmol) in DMF (35 ml) was added triethylamine (16 ml), then tetrakistriphenylphine palladium (0) (685 mg, 0.59 mmol) and copper(I) iodide (271 mg, 1.42 mmol) were added sequentially. Finally trimethylsilylacetylene (2.0 ml, 14.3 mmol) was added dropwise. The reaction mixture was stirred at 120° C. for 30 minutes and then directly adsorbed onto silica gel. Purification by flash chromatography on silica gel with a gradient of ethyl acetate/hexane afforded the title compound (2.30 g, 71% yield) as yellow oil. MS: m/z 270.0/272.0 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08268994B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-be220dfac195439ca94160734fad7b95 |
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| Source note | uspto-grants-2012_09 |
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