Sodium Hydroxide → HCID 68689034, compound

HRID 2238641Notes

Reaction equation

HRID 2238641 reaction equation
[C:1]([O:3][CH2:4][CH3:5])#[CH:2].B.O1CCCC1.Cl[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([S:20][CH3:21])[N:14]=1.[OH-].[Na+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([S:20][CH3:21])[N:14]=1)[CH3:2]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 61239Ether, ethyl ethynylHCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 68689034HCID 68689034, compoundYield 101.7%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

15 g of ethyl ethynyl ether (40% hexane solution) was dissolved in 50 mL of tetrahydrofuran, and 29 mL of a borane-tetrahydrofuran complex (1M tetrahydrofuran solution) was added to the solution at 0° C. After stirring at room temperature for 4 hours and a half, 150 mL of a tetrahydrofuran solution containing 4.0 g of the 4-chloro-6-methyl-2-(methylthio)pyrimidine [42-1], 35 mL of a 3 N aqueous solution of sodium hydroxide, 0.46 g of triphenylphosphine and 0.34 g of palladium acetate were added thereto. The obtained reaction solution was stirred at room temperature for 16 hours, and then 200 mL of water was added to the reaction solution. The reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated brine. After drying the organic layer over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and 4.9 g of 4-[(E)-2-ethoxyvinyl]-6-methyl-2-(methylthio)pyrimidine [42-2] was obtained as a brown oily product.

Workup

  1. additionwere added
  2. customThe obtained reaction solution
  3. stirringwas stirred at room temperature for 16 hours
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  7. filtrationthe insolubles were filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bf3e03de90b4131adcfda0df067dd91
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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