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

HRID 271554ノート

反応式

HRID 271554 の反応式
[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

参加物

9

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5be8e59fee24362b77d64a6ebe13980
出典データセット
uspto-grants-2008_11
特許番号
US07452886B2

反応ノート

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