Tributylvinyltin → HCID 178435592, compound

HRID 1708468Notes

Reaction equation

HRID 1708468 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC>C1(C)C=CC=CC=1.CN(C)C=O.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:17]=[CH2:18])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 178441862HCID 178441862, compound

Product 1

HCID 178435592HCID 178435592, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 12.28 g of 2-butyl-6-iodo-4(1H)-quinazolinone 0.866 g of tetrakis (triphenylphosphine)palladium, 0.015 g of 2,6-di-t-butyl-4-methylphenol in 75 ml of toluene and 20 ml of N,N-dimethylformamide is treated with 13.06 g of tri-n-butyl vinyltin followed by heating at reflux for 4 hours. The reaction mixture is cooled and concentrated in vacuo. The residue is diluted with hexanes and filtered. The filter cake is washed with hexanes and the remaining tacky solid dissolved in 100 ml of chloroform-methanol (8:2) and purified by chromato- graphy on silica gel with 1:3 ethyl acetate-hexanes to afford 4.55 g of the desired product as a yellow solid. CI MASS SPEC 229(MH+).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated in vacuo
  5. additionThe residue is diluted with hexanes
  6. filtrationfiltered
  7. washThe filter cake is washed with hexanes
  8. dissolutionthe remaining tacky solid dissolved in 100 ml of chloroform-methanol (8:2)
  9. custompurified by chromato- graphy on silica gel with 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-592bbdf3ada247a6b7c4949e9fdbf0d9
Source dataset
uspto-grants-1994_10
Patent number
US05358951

Reaction notes

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