Реакция #528084

Уравнение реакции

2-amino-3-cyano-5-ethynylpyrazine

4-trifluoromethylphenyl iodide

triethylamine

→

2-amino-3-cyano-5-[(4-trifluoromethylphenyl)ethynyl]pyrazine

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   ДругоеThe residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   ФильтрацияThe two-layered mixture is filtered
4. 4
   Другоеto remove a solid
5. 5
   ДругоеThe aqueous layer and the organic layer are separated
6. 6
   Промывкаthe aqueous layer is washed with ethyl acetate
7. 7
   ПромывкаThe ethyl acetate wash
8. 8
   Промывкаthe combination is washed with an aqueous solution of 10% lithium chloride
9. 9
   СушкаThe organic layer is dried with magnesium sulfate
10. 10
    Фильтрацияfiltered
11. 11
    КонцентрированиеThe filtrate is concentrated under reduced pressure to a residue
12. 12
    ДругоеThe residue is triturated with methylene chloride
13. 13
    Фильтрацияfiltered
14. 14
    ПромывкаElution
15. 15
    Концентрированиеconcentrated under reduced pressure

Методика

A solution of 3.2 grams (0.022 mole) of 2-amino-3-cyano-5-ethynylpyrazine, 8.4 grams (0.031 mole) of 4-trifluoromethylphenyl iodide, 10.7 grams (0.077 mole) of triethylamine, 0.5 gram (catalyst)of bis(triphenylphosphine)palladium(II) chloride, and 0.5 gram (catalyst) of copper iodide in 100 mL of acetonitrile is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid. The two-layered mixture is filtered to remove a solid. The aqueous layer and the organic layer are separated, and the aqueous layer is washed with ethyl acetate. The ethyl acetate wash is combined with the organic layer, and the combination is washed with an aqueous solution of 10% lithium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is triturated with methylene chloride and filtered. The filtrate is subjected to column chromatography on silica gel. Elution is accomplished using methanol/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-[(4-trifluoromethylphenyl)ethynyl]pyrazine.

Источник