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Cesium carbonate → 1-(2-Chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile

HRID 714815
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HRID 714815 반응식
[CH:1]1([C:4]2([C:10]#[N:11])[CH2:8][CH2:7][NH:6][C:5]2=[O:9])[CH2:3][CH2:2]1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Cl:12][C:13]1[N:18]=[C:17]([N:6]2[CH2:7][CH2:8][C:4]([CH:1]3[CH2:3][CH2:2]3)([C:10]#[N:11])[C:5]2=[O:9])[CH:16]=[CH:15][N:14]=1
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 775312,4-DichloropyrimidineHCID 916186313-Cyclopropyl-2-oxopyrrolidine-3-carbonitrile

생성물 1

HCID 1178398021-(2-Chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile수율 76.7%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

To a mixture of 3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile (18 g) obtained in Step C of Example 103, 2,4-dichloropyrimidine (17 g), cesium carbonate (76 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4.1 g) in tetrahydrofuran (300 mL) was added tris(dibenzylideneacetone)dipalladium(0) (2.1 g), and the mixture was stirred overnight at 85° C. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (23 g).

후처리

  1. customThe insoluble substance was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0407b204fb6046408ac3be18a6c0494b
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187453B2

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