1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline → 1-Benzo[1,3]dioxol-5-yl-2-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 2415360Notes

Reaction equation

HRID 2415360 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][C:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:26][N:25]=1>CN(C=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:25]=[CH:26][C:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)=[CH:28][N:29]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 27610202-Chloro-5-(4-methoxyphenyl)pyrimidine

Product 1

HCID 111236171-Benzo[1,3]dioxol-5-yl-2-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (2.72 g, 9.6 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24) and 2-chloro-5-(4-methoxyphenyl)pyrimidine (1.04 g, 4.78 mmol) were stirred in DMF (20 mL, anhydrous) at 120° C. for 16 h. The resulting mixture was quenched with saturated NH4Cl, extracted with ethyl acetate and dried with MgSO4. The reaction mixture solvent was evaporated and the residue purified by column chromatography (silica gel, ethyl acetate:hexanes=1:2) to yield the product as a white solid.

Workup

  1. customThe resulting mixture was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe reaction mixture solvent was evaporated
  5. customthe residue purified by column chromatography (silica gel, ethyl acetate:hexanes=1:2)

Sources & evidence

ORD record
ord-a0b00eefe7004ad496f59c6c4e0c4588
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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