Triethylamine → 2-Amino-3-cyano-5-(trimethylsilylethynyl)pyrazine

HRID 1683677노트

반응식

HRID 1683677 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5](Br)=[CH:4][N:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110526113-Amino-6-bromopyrazine-2-carbonitrile

생성물 1

HCID 153352712-Amino-3-cyano-5-(trimethylsilylethynyl)pyrazine

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

A solution of 3.0 grams (0.015 mole) of 2-amino-3-cyano-5-bromopyrazine and 2.1 grams (0.021 mole) of trimethylsilylacetylene in 50 mL of acetonitrile is stirred, and 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride are added in order. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. The reaction mixture is warmed to 70° C., where it is stirred for about 7.5 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is dissolved in ethyl acetate, and the solution is washed with 50 mL of aqueous, dilute hydrochloric acid. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. Elution is accomplished using tetrahydrofuran/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine.

후처리

  1. additionUpon completion of addition
  2. temperatureThe reaction mixture is warmed to 70° C.
  3. stirringwhere it is stirred for about 7.5 hours
  4. concentrationAfter this time, the reaction mixture is concentrated under reduced pressure to a residue
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe solution is washed with 50 mL of aqueous, dilute hydrochloric acid
  7. dry with materialThe organic layer is dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated under reduced pressure to a residue
  10. washElution
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6bd57e419e354636aacd348b30836777
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639753

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