Potassium Carbonate → 1-(5-Methoxy-pyridin-3-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80055

Reaction equation

HRID 80055 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:16]=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 8171633-Bromo-5-methoxypyridineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361521-(5-Methoxy-pyridin-3-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 9.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.847 mmol) was reacted with 3-bromo-5-methoxy-pyridine (159.24 mg, 0.847 mmol), 1,4-dioxane (15 mL), copper iodide (16.13 mg, 0.0847 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.254 mmol) and potassium carbonate (233.97 mg, 1.694 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform), followed by preparative HPLC afforded 23 mg of the product (9.55% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in chloroform)

Sources & evidence

ORD record
ord-fd88e67228384a0ca99867ce64dbf915
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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