반응 #528084

반응 방정식

2-amino-3-cyano-5-ethynylpyrazine

4-trifluoromethylphenyl iodide

triethylamine

→

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

용매

acetonitrile

반응 조건

후처리

1. 1
   농축After this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   기타The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   여과The two-layered mixture is filtered
4. 4
   기타to remove a solid
5. 5
   기타The aqueous layer and the organic layer are separated
6. 6
   세척the aqueous layer is washed with ethyl acetate
7. 7
   세척The ethyl acetate wash
8. 8
   세척the combination is washed with an aqueous solution of 10% lithium chloride
9. 9
   건조The organic layer is dried with magnesium sulfate
10. 10
    여과filtered
11. 11
    농축The filtrate is concentrated under reduced pressure to a residue
12. 12
    기타The residue is triturated with methylene chloride
13. 13
    여과filtered
14. 14
    세척Elution
15. 15
    농축concentrated under reduced pressure

실험 절차

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.

출처