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

HRID 2415364
Notes
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Reaction equation

HRID 2415364 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c4a98c7fb7f74426a404c5aa7914603c
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06818646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes