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ChemicalBook CAS DataBase List 2-ethynylpyrazine
153800-11-4

2-ethynylpyrazine synthesis

2synthesis methods
2-[2-(trimethylsilyl)ethynyl]pyrazine

291763-66-1

2-ethynylpyrazine

153800-11-4

To a solution of compound (CAS:291763-66-1) (3.0 g, 17.02 mmol) in THF (10 mL) was slowly added 1 M TBAF (tetrabutylammonium fluoride) solution over 9 min. The progress of the reaction was monitored by TLC (Thin Layer Chromatography) to confirm the complete conversion of the feedstock to the target product 2-alkynylpyrazines. After completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography to give 2-alkynylpyrazines (1.0 g, yield: 56.5%). LC-MS (Liquid Chromatography-Mass Spectrometry) analysis showed: m/z 105 ([M+H]+).

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Yield: 56.5%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran for 0.05 h;

Steps:

3 Procedure for preparation of2ethyny1pyraziaie:
To a solution of 9(3.Og, 17.O2rnrnoi) in iOmL THE was added IM of TBAF over 3 minutes. TLC analysis showed complete conversion of starting material to a major product. The reactionmixture was then concentrated in vacuo. The crude product was purified by silica gel column chromatography to give product 10(1.0g. yield: 56.5%).LCMS: m/ 105 (M+H).

References:

HUA MEDICINE (SHANGHAI) LTD.;CHEN, Li;JIN, Xiaowei WO2017/117708, 2017, A1 Location in patent:Page/Page column 18; 19