反应 #528084

反应方程式

2-amino-3-cyano-5-ethynylpyrazine

4-trifluoromethylphenyl iodide

triethylamine

→

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

溶剂

acetonitrile

反应条件

后处理

1. 1
   浓缩After this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   其他The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   过滤The two-layered mixture is filtered
4. 4
   其他to remove a solid
5. 5
   其他The aqueous layer and the organic layer are separated
6. 6
   洗涤the aqueous layer is washed with ethyl acetate
7. 7
   洗涤The ethyl acetate wash
8. 8
   洗涤the combination is washed with an aqueous solution of 10% lithium chloride
9. 9
   干燥The organic layer is dried with magnesium sulfate
10. 10
    过滤filtered
11. 11
    浓缩The filtrate is concentrated under reduced pressure to a residue
12. 12
    其他The residue is triturated with methylene chloride
13. 13
    过滤filtered
14. 14
    洗涤Elution
15. 15
    浓缩concentrated under reduced pressure

实验过程

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.

来源