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

HRID 601657ノート

反応式

HRID 601657 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-53dd503f7b9c44f78feb09172bb84bf7
出典データセット
uspto-grants-2011_03
特許番号
US07902369B2

反応ノート

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