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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
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HRID 271600 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-3a141206a4fd45a5a99114a39c48938b
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452886B2

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