Pyridine → HCID 57460906, compound

HRID 1718928Notes

Reaction equation

HRID 1718928 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:26])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1.[O:27]1[CH2:32][CH2:31][CH:30]([O:33][C:34]2[N:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)[CH2:29][CH2:28]1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.C(Cl)Cl>[CH3:1][C:2]1[N:3]([C:37]2[CH:38]=[N:39][C:34]([O:33][CH:30]3[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)=[CH:35][CH:36]=2)[C:4](=[O:26])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 59469479{6-[(Oxan-4-yl)oxy]pyridin-3-yl}boronic acidHCID 1354272734'-[(2-Methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 57460906HCID 57460906, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.5 g), [6-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-yl]boronic acid (0.49 g), copper acetate (0.53 g), pyridine (0.6 mL), triethylamine (1 mL), molecular sieves 4 A (1 g) and methylene chloride (10 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 amorphous solid (0.25 g, 33%).

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-b321dbcff73144c68aa012798bfd5797
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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