Stannane, tributyl(1-ethoxyethenyl)- → HCID 117696387, compound

HRID 2205288Notes

Reaction equation

HRID 2205288 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:21]([O:20][C:18]([C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)=[CH2:19])[CH3:22]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 181856184-Chloro-8-methylquinazoline

Product 1

HCID 117696387HCID 117696387, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

4-Chloro-8-methylquinazoline (5.10 g, 25.13 mmol) is dissolved in toluene (50 mL) and tributyl(1-ethoxyvinyl)tin (9.98 g, 27.64 mmol) and tetrakis(triphenylphosphine) palladium(0) (1.45 g, 1.26 mmol) are added to the solution and the reaction is refluxed for 3 h. Volatiles are evaporated under reduced pressure and the resulting mixture is diluted with brine and ethyl acetate. The phases separated and the organic phase washed with brine, dried and volatiles evaporated under reduced pressure. The residue is purified by flash chromatography (0-30% EtOAc in cyclohexane) to give 4-(1-ethoxy-vinyl)-8-methyl-quinazoline (4.80 g, 89%).

Workup

  1. temperaturethe reaction is refluxed for 3 h
  2. customVolatiles are evaporated under reduced pressure
  3. additionthe resulting mixture is diluted with brine and ethyl acetate
  4. customThe phases separated
  5. washthe organic phase washed with brine
  6. customdried
  7. customvolatiles evaporated under reduced pressure
  8. customThe residue is purified by flash chromatography (0-30% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-2e2218a33e4c4625af3037f3ea44397e
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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