Pyridine → HCID 57460490, compound

HRID 1673917Notes

Reaction equation

HRID 1673917 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[N:5][C:4]([CH2:8][CH2:9][CH3:10])=[C:3]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1.[CH:26]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([CH3:28])[CH3:27].C(N(CC)CC)C.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.C(Cl)Cl>[CH:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:7]2[C:2](=[O:1])[C:3]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:14][CH:13]=3)=[C:4]([CH2:8][CH2:9][CH3:10])[N:5]=[CH:6]2)=[CH:32][CH:31]=1)([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 36987264-Isopropoxybenzeneboronic acidHCID 135464158HCID 135464158, compound

Product 1

HCID 57460490HCID 57460490, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-[(6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1.02 g), (4-isopropoxyphenyl)boronic acid (0.65 g), molecular sieves 4 A (1.98 g), triethylamine (1.7 mL), pyridine (1.0 mL), copper(II) acetate (0.65 g) and methylene chloride (15 mL) was stirred at room temperature for 24 hr. Ethyl acetate was added to the reaction mixture, and the insoluble solid was filtered off. The solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.62 g, 44%).

Workup

  1. filtrationthe insoluble solid was filtered off
  2. customThe solvent of the filtrate was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1bcaf27409b446c2961b447c082dd2d0
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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