Triethylamine → 6-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271554노트

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HRID 271554 반응식
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[C:2]#[CH:3].Br[C:10]1[C:11]([NH:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1.C(N(CC)CC)C>CN(C=O)C.O.CCOC(C)=O.[Cu]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>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][N:18]1[C:11]2[N:12]=[C:13]([C:16]#[N:17])[N:14]=[CH:15][C:10]=2[CH:3]=[C:2]1[CH2:1][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1

참가 물질

9

반응물 3

HCID 8471TriethylamineHCID 125919421-(prop-2-yn-1-yl)-1H-imidazoleHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile

생성물 1

HCID 99439696-((1H-imidazol-1-yl)methyl)-7-neopentyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile수율 64%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

1-Prop-2-ynyl-1H-imidazole (15 mmol) is dissolved in DMF at room temperature under nitrogen atmosphere. To the solution, 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (8 mmol), triethylamine (24 mmol), copper(I) iodide (0.8 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.4 mmol) are added successively. The mixture is heated at 80° C. under nitrogen atmosphere for 3 h. After cooling at room temperature, the mixture is diluted with H2O and AcOEt and filtered with celite. The organic layer is taken, dried over MgSO4 and evaporated in vacuo. The residue is purified by silica gel column chromatography (AcOEt:MeOH=20:1) to give 7-(2,2-dimethyl-propyl)-6-imidazol-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 64% yield.

후처리

  1. temperatureAfter cooling at room temperature
  2. filtrationfiltered with celite
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue is purified by silica gel column chromatography (AcOEt:MeOH=20:1)

출처 및 근거

ORD 기록
ord-b5be8e59fee24362b77d64a6ebe13980
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452886B2

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