Dimethylformamide → 1,2,3,4-Tetrahydro-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

HRID 988308Notes

Reaction equation

HRID 988308 reaction equation
[H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH:12]3[C:24]4[NH:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16]=4[CH2:15][CH2:14][N:13]3[C:25]3[N:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)=[CH:27][N:26]=3)=[CH:6][C:5]=2[O:4]1.CN(C=[O:45])C>>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:28]2[CH:29]=[N:30][C:25]([N:13]3[CH2:14][C:15]4[C:16](=[O:45])[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[NH:23][C:24]=4[CH:12]3[C:7]3[CH:8]=[CH:9][C:10]4[O:11][CH2:3][O:4][C:5]=4[CH:6]=3)=[N:26][CH:27]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 110494301-Benzo[1,3]dioxol-5-yl-2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 103016221,2,3,4-Tetrahydro-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Procedure

Sodium hydride (60% in mineral oil, 40 mg, 1.0 mmol) and 1-(3,4-methylenedioxyphenyl)-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline (218 mg, 0.43 mmol) (prepared as in Example 13) in DMF (10 mL, anhydrous) were stirred at room temperature for 30 min. Dry air was then bubbled through the solution for 16 h. Ethyl acetate (100 mL) and saturated NaHCO3 were added, the organic phase was washed with water, brine, and dried with MgSO4. Solvent was evaporated and the residue purified by chromatography (silica gel, ethyl acetate) to yield the product as a white solid.

Workup

  1. customDry air
  2. customwas then bubbled through the solution for 16 h
  3. additionEthyl acetate (100 mL) and saturated NaHCO3 were added
  4. washthe organic phase was washed with water, brine
  5. dry with materialdried with MgSO4
  6. customSolvent was evaporated
  7. customthe residue purified by chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-37f5c5b3f8044fb889ae2eaff6ac1f79
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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