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Cesium carbonate → 3-(4-Tert-butylphenyl)-1-({2-[(6-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 546628
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HRID 546628 반응식
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([CH2:9][N:10]2[C:14]([CH3:16])([CH3:15])[C:13](=[O:17])[N:12]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=3)[C:11]2=[O:28])[CH:6]=[CH:5][N:4]=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][N:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([N:12]2[C:13](=[O:17])[C:14]([CH3:16])([CH3:15])[N:10]([CH2:9][C:7]3[CH:6]=[CH:5][N:4]=[C:3]([NH:2][C:33]4[CH:32]=[N:31][C:30]([Cl:29])=[CH:35][CH:34]=4)[CH:8]=3)[C:11]2=[O:28])=[CH:23][CH:22]=1)([CH3:27])([CH3:26])[CH3:25]
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 43971762-Chloro-5-iodopyridineHCID 671984711-[(2-Aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochlorideHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)

생성물 1

HCID 576259803-(4-Tert-butylphenyl)-1-({2-[(6-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 0.5 g of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride obtained in stage c) of Example 7 in 35 mL of dioxane are successively added under argon 0.39 g of 2-chloro-5-iodopyridine, 1.8 g of caesium carbonate, 947 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (xantphos) and 30 mg of palladium diacetate. The reaction mixture is heated at 90° C. for 3 hours and then filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of cyclohexane and ethyl acetate (62/38 by volume) to give 0.368 g of 3-(4-tert-butylphenyl)-1-({2-[(6-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by chromatography on a column of silica
  4. washeluting with a mixture of cyclohexane and ethyl acetate (62/38 by volume)

출처 및 근거

ORD 기록
ord-b02d4efb0f484eeeab9693a0d66f3471
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935819B2

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