Trimethylsilylacetylene → HCID 178441850, compound

HRID 1975662Notes

Reaction equation

HRID 1975662 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].[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>CN(C)C=O.C(N(CC)CC)C.[Pd](Cl)Cl.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.[Cu]I>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178441862HCID 178441862, compound

Product 1

HCID 178441850HCID 178441850, compoundYield 82.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1.0 g of 2-butyl-6-iodo-4(1H)-quinazolinone 0.043 g of bis(triphenylphosphine) palladium (II) chloride and 5.8 mg of copper (I) iodide in 5.0 ml of N,N-dimethylformamide and 5.0 ml of triethylamine is added 0.36 g of (trimethylsilyl) acetylene. The resulting reaction mixture is heated at 45° C. for 1 hour and then 65° C. for 5 hours. Upon cooling, the reaction mixture is concentrated in vacuo and the residue purified by flash chromatography on silica gel, eluting with 1:3 ethyl acetate-hexane to yield 0.75 g of the desired product as a white solid. CI MASS SPEC 299(MH+).

Workup

  1. customThe resulting reaction mixture
  2. temperatureUpon cooling
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. customthe residue purified by flash chromatography on silica gel
  5. washeluting with 1:3 ethyl acetate-hexane

Sources & evidence

ORD record
ord-6a565cbe59214ae1a7d7c33eb5833cc1
Source dataset
uspto-grants-1994_02
Patent number
US05288720

Reaction notes

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