Tributylvinyltin → HCID 57460560, compound

HRID 1673985Notes

Reaction equation

HRID 1673985 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH2:32][CH3:33])[N:10]=[C:9]2[CH3:34])[CH:5]=[CH:6][CH:7]=1.[CH:35]([Sn](CCCC)(CCCC)CCCC)=[CH2:36].[Cl-].[Li+].[F-].[K+]>CN(C)C=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:30]([C:11]1[N:10]=[C:9]([CH3:34])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:35]=[CH2:36])[CH:3]=2)[C:13](=[O:14])[C:12]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 4

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 57460559HCID 57460559, compound

Product 1

HCID 57460560HCID 57460560, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 4′-{[1-(3-bromophenyl)-4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (1.0 g), vinyltributyltin (0.86 mL), dichlorobis(triphenylphosphine)palladium(II) and lithium chloride (0.25 g) in N,N-dimethylformamide (10 mL) was stirred at 90° C. for 3 hr under an argon atmosphere. The mixture was allowed to cool to room temperature, 20% aqueous potassium fluoride solution was added, and the mixture was stirred for 12 hr. The reaction mixture was diluted with ethyl acetate, and the insoluble material was filtered off through celite. The filtrate was washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.45 g, 50%).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred for 12 hr
  3. filtrationthe insoluble material was filtered off through celite
  4. washThe filtrate was washed with water
  5. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-89eb137a7254474d8f259a45298127be
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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