2-Bromonaphthalene → HCID 59636271, compound

HRID 2383850Notes

Reaction equation

HRID 2383850 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]1=[O:14].Br[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[C:9]1=[O:14]

Participants

7

Reactant 4

HCID 113722-BromonaphthaleneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 687848891-(4-Methyl-pyridin-3-yl)-tetrahydro-pyrimidin-2-one

Product 1

HCID 59636271HCID 59636271, compoundYield 26.2%

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)-tetrahydro-pyrimidin-2-one (I-130b: 150 mg, 0.785 mmol) was reacted with 2-bromo-naphthalene (195 mg, 0.942 mmol), 1,4-dioxane (20 mL), copper iodide (15 mg, 0.078 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.235 mmol) and potassium phosphate (415 mg, 1.96 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3), followed by recrystallization using DCM and hexane afforded 65 mg of the product (26.2% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)
  3. customfollowed by recrystallization

Sources & evidence

ORD record
ord-0cfd9ad5ac474f918444e221c969976f
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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