2-Bromonaphthalene → 1-Naphthalen-2-yl-3-pyridin-3-yl-tetrahydro-pyrimidin-2-one

HRID 80033Notes

Reaction equation

HRID 80033 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:12][CH2:11][CH2:10][NH:9][C:8]2=[O:13])[CH:2]=1.Br[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:21]1[C:22]2[C:17](=[CH:16][CH:15]=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[N:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8]1=[O:13]

Participants

7

Reactant 4

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 59636159HCID 59636159, compound

Product 1

HCID 596362151-Naphthalen-2-yl-3-pyridin-3-yl-tetrahydro-pyrimidin-2-oneYield 35.71%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-tetrahydro-pyrimidin-2-one (I-10b: 118 mg, 0.724 mmol) was reacted with 2-bromo-naphthalene (150 mg, 0.724 mmol), 1,4-dioxane (5 mL), copper iodide (13.79 mg, 0.0724 mmol), trans-1,2-diamino cyclohexane (24.865 mg, 0.2172 mmol) and potassium carbonate (200 mg, 1.448 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 75 mg of the product (35.71% 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-268c04b1e14c42b48aaeb2e69afaef06
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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