Potassium Iodide → 5-(tert-butoxycarbonylmethoxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-1,2,3,4-tetrahydronaphthalene

HRID 1271297Notes

Reaction equation

HRID 1271297 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:21][CH:22]3[CH2:31][CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]=4[OH:32])[CH2:23]3)[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:38]([O:37][C:35]([CH2:34][O:32][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:29]=1[CH2:30][CH2:31][CH:22]([CH2:21][N:19]([C:10]1[CH:9]=[N:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=1)[CH3:20])[CH2:23]2)=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 184526502-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-5-hydroxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 184526595-(tert-butoxycarbonylmethoxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-1,2,3,4-tetrahydronaphthaleneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 413 mg of 2-[N-(5,6-diphenylpyrazin-2-yl)-N-methyl(aminomethyl)]-5-hydroxy-1,2,3,4-tetrahydronaphthalene and 210 mg of tert-butyl bromoacetate in 10 ml of acetonitrile, a catalytic amount of potassium iodide and 163 mg of potassium carbonate were added and the mixture was heated at reflux for 4 hours. The insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 423 mg of the desired compound as a pale orange oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30d019179ffb42ffa6d2c10eba62df76
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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