ChemicalBook CAS DataBase List 2-Methyl-5-vinylpyrazine, 99%

2-Methyl-5-vinylpyrazine, 99% synthesis

7synthesis methods

Product Name:2-Methyl-5-vinylpyrazine, 99%
CAS Number:13925-08-1
Molecular formula:C7H8N2
Molecular Weight:120.15

By methylation of the Mannich base obtained by reacting formaldehyde and dimethylamine with dimethyl-2,5-pyrazine, followed by the Hoffman degradation

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Yield: 71%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 20 - 100;Inert atmosphere;

Steps:

11
Example 11 Preparation of 2-methyl-5-vmyl-pyrazme[0376] The title compound was prepared by following general procedure 2 5-Bromo-2- methyl pyrazme (2 0 g, 11 mmol) was dissolved in DMF THF (3 1 , 24 mL) Tϖbutylvmyltm (3 0 g, 12 6 mmol) and Pd(PPh₃)₄ (0 172 g, 0 143 mmol) was added to this solution at RT under nitrogen and was heated at 100 ⁰C for 3 h The reaction mixture was cooled to RT and diluted with water (240 mL) and extracted with ethyl acetate (3x150 mL), the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure below 40° C The crude was purified through column chromatography (2% ethylacetate hexane in silica 100- 200 mesh, Diameter of column - 5 0 cm, Height of silica - approx 5 inch) to provide 2-methyl- 5-vmylpyrazme as a light yellow oil (1 0 g, 71% yield)

References:

MEDIVATION TECHNOLOGIES, INC.;HUNG, David, T.;PROTTER, Andrew, Asher;JAIN, Rajendra, Parasmal;CHAKRAVARTY, Sarvajit;GIORGETTI, Marco WO2010/51503, 2010, A1 Location in patent:Page/Page column 250-251