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2-Chloropyrimidine → 1-(3,4-Methylenedioxvphenyl)-2-(pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 988306
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HRID 988306 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][NH:11]3)=[CH:4][C:3]=2[O:2]1.Cl[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:4][C:3]=2[O:2]1
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참가 물질

5

반응물 2

HCID 744042-ChloropyrimidineHCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

생성물 1

HCID 109815071-(3,4-Methylenedioxvphenyl)-2-(pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (2.3 g, 8.0 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24) and 2-chloropyrimidine (0.914 g, 8.0 mmol) were stirred in anhydrous DMF (15 mL) at 140° C. for 24 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated aqueous NH4Cl solution (100 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (2×80 mL) and dried with MgSO4. The solvents were evaporated and the product was isolated by column chromatography (silica gel, EtOAc:Hexane=1:9 ) as a yellowish solid.

후처리

  1. washwashed with saturated aqueous NH4Cl solution (100 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with brine (2×80 mL)
  4. dry with materialdried with MgSO4
  5. customThe solvents were evaporated
  6. customthe product was isolated by column chromatography (silica gel, EtOAc:Hexane=1:9 ) as a yellowish solid

출처 및 근거

ORD 기록
ord-2ae60a61dfaa4703bc3a92123f4c78ca
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06635638B2

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