2-(Tributylstannyl)pyridine → HCID 178517958, compound

HRID 2225182Notes

Reaction equation

HRID 2225182 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[OH:12].C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC>C1(C)C=CC=CC=1.CN(C=O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[OH:12]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 178517953HCID 178517953, compound

Product 1

HCID 178517958HCID 178517958, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Preparation D12, Step 2: A mixture of 6-bromoquinazolin-4-ol (173 mg, 0.77 mmol) and 2-tributylstannylpyridine (850 mg, 2.30 mmol) in toluene (10 mL), plus a few drops of DMF to improve solubility, was degassed under vacuum/argon, then a catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added, the mixture was degassed again, and then heated at reflux for 4 h. The reaction was cooled to room temperature, and some solids were removed by filtration. Analysis by LC/MS indicated that the desired product was present in both the solids and the filtrate. The solids were slurried in 8:2 methylene chloride/methanol, the mixture was filtered, the filtrate was combined with the original filtrate, and this mixture was concentrated in-vacuo. The residue was purified over silica gel, eluting with 50% EtOAc/hexanes, 75% EtOAc/hexanes, 100% EtOAc, 5% MeOH/EtOAc, to yield 106 mg of 6-(pyridin-2-yl)quinazolin-4-ol as a colorless solid. MS (ES+)=224 (M+H+).

Workup

  1. customPreparation D12, Step 2
  2. customwas degassed under vacuum/argon
  3. additiona catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added
  4. customthe mixture was degassed again
  5. temperatureheated
  6. temperatureat reflux for 4 h
  7. customsome solids were removed by filtration
  8. filtrationthe mixture was filtered
  9. concentrationthis mixture was concentrated in-vacuo
  10. customThe residue was purified over silica gel
  11. washeluting with 50% EtOAc/hexanes, 75% EtOAc/hexanes, 100% EtOAc, 5% MeOH/EtOAc

Sources & evidence

ORD record
ord-156703e7f97240ffb53aa6c6c49dc4f3
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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