Triethylamine → 3-Benzyl-4-oxo-6-(2-trimethylsilylethynyl)-3,4-dihydroquinazoline

HRID 601657Notes

Reaction equation

HRID 601657 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH2:14]([N:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27](Br)[CH:28]=2)[N:23]=[CH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Cu](I)I.[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.CN(C)C=O>[CH2:14]([N:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:28]=2)[N:23]=[CH:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11875073-benzyl-6-bromoquinazolin-4(3H)-one

Product 1

HCID 231582983-Benzyl-4-oxo-6-(2-trimethylsilylethynyl)-3,4-dihydroquinazolineYield 107.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen atmosphere, 947 mg of trimethylsilylacetylene, 54.7 mg of copper iodide (I), 54.2 mg bis(triphenylphosphine) palladium dichloride (II) and 3 ml of triethylamine were added sequentially to 1.5 ml solution of dimethylformamide with 501 mg of 3-benzyl-6-bromo4-oxo-3,4-dihydroquinazoline, and the mixture was stirred at 100° C. for 14 hours. After distilling out the solvents under reduced pressure, water was added to the reaction solution, and extracted with ether. Ether layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=3/7) to obtain 570 mg of the above compound as a colorless oily matter.

Workup

  1. distillationAfter distilling out the solvents under reduced pressure, water
  2. additionwas added to the reaction solution
  3. extractionextracted with ether
  4. washEther layer was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solvents were distilled outunder reduced pressure
  7. customthe residues were separated
  8. custompurified by silicagel column chromatography (ethyl acetate/hexane=3/7)

Sources & evidence

ORD record
ord-53dd503f7b9c44f78feb09172bb84bf7
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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