Tributylstannane → HCID 135724439, compound

HRID 1828437Notes

Reaction equation

HRID 1828437 reaction equation
Br[C:2]1[C:6]([CH2:7][CH3:8])=[CH:5][S:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:22]=[CH:21][N:14]2[C:15](=[O:20])[CH:16]=[C:17]([OH:19])[N:18]=[C:13]2[CH:12]=1.C([SnH](CCCC)CCCC)CCC.[F-].[K+]>C1(C)C=CC=CC=1>[CH2:7]([C:6]1[CH:2]=[C:3]([CH2:9][CH2:10][C:11]2[CH:22]=[CH:21][N:14]3[C:15](=[O:20])[CH:16]=[C:17]([OH:19])[N:18]=[C:13]3[CH:12]=2)[S:4][CH:5]=1)[CH3:8]

Participants

5

Reactant 3

HCID 5948Tributylstannane3×HCID 522689Potassium FluorideHCID 135724441HCID 135724441, compound

Product 1

HCID 135724439HCID 135724439, compoundYield 158.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

8-[2-(3-Bromo-4-ethyl-2-thienyl)ethyl]-2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one (96 mg, 0.25 mmol) dissolved in toluene (6 ml) was added with tributyltin hydride (75 μl) and 2,2-azobisisobutyronitrile (4 mg, 0.025 mmol) and refluxed by heating at 140° C. Then 2,2-azobisisobutyronitrile and tributyltin hydride were further added until the reaction was completed while the progress of the reaction was monitored by LC-MS. 34 mg (0.22 mmol) of 2,2-azobisisobutyronitrile and 350 μl (1.30 mmol) of tributyltin hydride were used. The reaction solution was returned to room temperature and the reaction was stopped with an aqueous solution of potassium fluoride. The reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated brine. Then, the aqueous layer was extracted with ethyl acetate. The organic layer collected was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1) to obtain 119 mg of the title compound with contained impurities.

Workup

  1. temperaturerefluxed
  2. customwas returned to room temperature
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. extractionThen, the aqueous layer was extracted with ethyl acetate
  6. customThe organic layer collected
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-81943952658e4a039987ed8a40cf13fc
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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