5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine

5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Property

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

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Chemical Properties,Usage,Production

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