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Triethylamine → 4-[2-Cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-benzoic acid

HRID 271600
ノート
印刷プレビュー

反応式

HRID 271600 の反応式
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[C:2]#[CH:3].Br[C:14]1[C:15]([NH:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:16][C:17]([C:20]#[N:21])=[N:18][CH:19]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=O)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>[C:20]([C:17]1[N:18]=[CH:19][C:14]2[CH:3]=[C:2]([CH2:1][C:4]3[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=3)[N:22]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]=2[N:16]=1)#[N:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrileHCID 227233984-(Prop-2-YN-1-YL)benzoic acid

生成物 1

HCID 598346554-[2-Cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-benzoic acid収率 51%

試薬・触媒・溶媒 3

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

反応条件

温度
75 °C

実験手順

To a solution of 4-prop-2-ynyl-benzoic acid (6.3 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (4.8 mmol) in DMF (30 ml), triethylamine(14.4 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.48 mmol) and copper (I) iodide (0.96 mmol) are added. The reaction mixture is heated at 75° C. ca. for 18 h. Saturated aqueous solution of ammonium chloride is added to the reaction mixture and then aqueous layer is extracted with two 150 ml portions of AcOEt. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude product which is purified by silica gel column chromatography. Yield: 51%. Rf=0.18 (AcOEt only)

後処理

  1. extractionaqueous layer is extracted with two 150 ml portions of AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give crude product which
  6. customis purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3a141206a4fd45a5a99114a39c48938b
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07452886B2

反応ノート

読み込み中…

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