53593-61-6 → HCID 178435592, compound

HRID 1974934Notes

Reaction equation

HRID 1974934 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].[CH:17]([Sn])=[CH2:18]>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 1106253753593-61-6HCID 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 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 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 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 chromatography on silica gel with 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-de8131d8878c46c5a19e627d51589a4b
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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