Indoline → HCID 57390025, compound

HRID 2278647Notes

Reaction equation

HRID 2278647 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.[N:14]1([C:20]2[N:21]=[C:22]([CH2:33][C:34](OCC)=[O:35])[N:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24](=[O:26])[CH:25]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C1(C)C=CC=CC=1.O1CCCC1>[N:1]1([C:34](=[O:35])[CH2:33][C:22]2[N:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:24](=[O:26])[CH:25]=[C:20]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10328IndolineHCID 16682925TrimethylaluminumHCID 86699281HCID 86699281, compound

Product 1

HCID 57390025HCID 57390025, compoundYield 3.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

56 mg of indoline and 0.36 ml of 2M trimethyl aluminum in toluene are successively added to a solution of 65 mg of ethyl (4-morpholin-4-yl-6-oxo-1-phenyl-1,6-dihydropyrimidin-2-yl)acetate in 3 ml of tetrahydrofuran and 1.5 ml of toluene. The reaction mixture is heated at 90° C. for 4 hours and then concentrated under reduced pressure. The residue is purified twice by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (98/2, V/V) and then with ethyl acetate, so as to give 3 mg of 2-[2-(2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3-phenyl-3H-pyrimidin-4-one in the form of a solid, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified twice by silica column chromatography, elution
  3. additionbeing carried out with a mixture of dichloromethane and methanol (98/2, V/V)

Sources & evidence

ORD record
ord-66d9a98bb3ea45bd93d2f071e4ff2166
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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