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| | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Basic information |
| Product Name: | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine | | Synonyms: | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine;5-broMo-3-(2-(triMethylsilyl)ethynyl)pyrazin-2-aMine;Pyrazinamine, 5-bromo-3-[(trimethylsilyl)ethynyl]-;5-bromo-3-[2-(trimethylsilyl)ethynyl]-2-Pyrazinamine;5-Bromo-3-((trimethylsilyl);EOS-61575;5-Bromo-3-trimethylsilanylethynylpyrazin-2-ylamine;2-Pyrazinamine, 5-bromo-3-[2-(trimethylsilyl)ethynyl]- | | CAS: | 875781-41-2 | | MF: | C9H12BrN3Si | | MW: | 270.2 | | EINECS: | | | Product Categories: | | | Mol File: | 875781-41-2.mol |  |
| | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Chemical Properties |
| Boiling point | 313.8±42.0 °C(Predicted) | | density | 1.39±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 1.78±0.10(Predicted) | | Appearance | Yellow to brown Solid | | InChI | InChI=1S/C9H12BrN3Si/c1-14(2,3)5-4-7-9(11)12-6-8(10)13-7/h6H,1-3H3,(H2,11,12) | | InChIKey | LQJGZEFWBXJKJI-UHFFFAOYSA-N | | SMILES | C1(N)=NC=C(Br)N=C1C#C[Si](C)(C)C |
| | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Usage And Synthesis |
| Synthesis | To a solution of 3,5-dibromopyrazin-2-amine (2.00 g, 7.91 mmol) in anhydrous THF (24 mL) was sequentially added triethylamine (3.3 mL, 24 mmol), cuprous iodide (151 mg, 0.79 mmol), and Pd(PPh3)2Cl2 (catalytic amount). The reaction mixture was cooled to -5 °C under nitrogen protection, and then trimethylsilylacetylene (1.07 mL, 7.50 mmol) was slowly added dropwise. After the dropwise addition, the reaction system was slowly warmed to 0 °C and stirred at this temperature for 1.5 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent, and the resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 5:1, v/v) to afford the target product, 3-[(trimethylsilyl)alkynyl]-5-bromopyrazin-2-amine, as a black oily substance (42 mg, 94% yield). Mass spectrum (ESI, positive ion mode) m/z: 272.00 [M + H]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.04 (s, 1H), 5.14 (s, 2H), 0.30 (s, 9H). | | References | [1] Patent: WO2018/108125, 2018, A1. Location in patent: Paragraph 00586
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 693 - 698
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4399 - 4404
[4] Patent: CN106432246, 2017, A. Location in patent: Paragraph 0540; 0541; 0542
[5] Patent: WO2010/54398, 2010, A1. Location in patent: Page/Page column 150-151 |
| | 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Preparation Products And Raw materials |
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