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Pyrimidine, 2,4-dichloro-5-methyl- → 1-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

HRID 592433
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HRID 592433 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]1)#[CH:2].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([CH3:23])=[CH:18][N:17]=1>O1CCOCC1.[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>[Cl:15][C:16]1[N:21]=[C:20]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]2)[C:19]([CH3:23])=[CH:18][N:17]=1
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6

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HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 867122761-(2-Ethynylphenyl)cyclopropanecarboxamide

생성물 1

HCID 867123141-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of 1-(2-ethynylphenyl)cyclopropanecarboxamide K6 (2.29 g, 12.4 mmol), 2,4-dichloro-5-methylpyrimidine (2.62 g, 16.1 mmol), CuI (0.047 g, 0.25 mmol) and PdCl2(PPh3)2 (0.087 g, 0.12 mmol) in dioxane (25 mL) was bubbled with N2 for 10 minutes. Et3N (10 mL) was added and the mixture was stirred under nitrogen at 70° C. for 1 hour. The reaction mixture was cooled and adsorbed onto silica. Purification by column chromatography (Biotage Isolera, 120 g SiO2, 0-10% MeOH in CHCl3) gave the title compound A39 as a yellow oil (1.85 g, 48%). LCMS-D: rt 3.24 min; m/z 312 [M+H]+.

후처리

  1. customwas bubbled with N2 for 10 minutes
  2. additionEt3N (10 mL) was added
  3. temperatureThe reaction mixture was cooled
  4. customPurification by column chromatography (Biotage Isolera, 120 g SiO2, 0-10% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-a3d6234abfbe40be84b48befb5e708ff
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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