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

HRID 1465033ノート

反応式

HRID 1465033 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a36e33a791074d14a69a0490b9d346bd
出典データセット
uspto-grants-2015_04
特許番号
US08999973B2

反応ノート

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