Tributylvinyltin → HCID 178435592, compound

HRID 486499Notes

Reaction equation

HRID 486499 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-reethanol (8:2) and purified by chromatography 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 229MH+).

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-reethanol (8:2)
  9. custompurified by chromatography on silica gel with 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-73cc92bf5e844525940374eb5723dc58
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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