Nitrogen → 4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine

HRID 1465033노트

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HRID 1465033 반응식
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=2[S:4][CH:3]=1.C1(NC2CCCCC2)CCCCC1.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].N#N>C(#N)C.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.[Cu]I>[CH3:12][S:11][C:10]1[C:5]2[S:4][CH:3]=[C:2]([C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:6]=2[N:7]=[CH:8][N:9]=1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 7582DicyclohexylamineHCID 66111TrimethylsilylacetyleneHCID 469284277-Bromo-4-methylsulfanylthieno[3,2-d]pyrimidine

생성물 1

HCID 673274394-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine수율 65.6%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

7-Bromo-4-(methylthio)thieno[3,2-d]pyrimidine (3 g, 11.49 mmol) was dissolved in acetonitrile (30 mL) and then bis(triphenylphosphine)palladium(II) dichloride (204 mg, 0.29 mmol), CuI (76 mg, 0.40 mmol), dicyclohexylamine (2.5 mL, 12.64 mmol) and ethynyltrimethylsilane (3.2 mL, 22.98 mmol) were added thereto. The reaction mixture was treated with N2 gas for 15 minutes and stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature, filtered using Celite and washed with ethyl acetate (50 mL). The filtrate was washed with brine and concentrated by drying with MgSO4. The resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=1:9˜2:8) to obtain the title compound (2.1 g, 65% yield) as a yellowish solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with ethyl acetate (50 mL)
  4. washThe filtrate was washed with brine
  5. concentrationconcentrated
  6. dry with materialby drying with MgSO4
  7. customThe resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=1:9˜2:8)

출처 및 근거

ORD 기록
ord-a36e33a791074d14a69a0490b9d346bd
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999973B2

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