Triethylamine → 1-(4-Chlorobenzyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2(1H)-one

HRID 1477680ノート

反応式

HRID 1477680 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:4](=[O:16])[N:3]=1.C(N(CC)CC)C.[CH3:24][C:25]1([CH3:38])[C:29]([CH3:31])([CH3:30])[O:28][B:27]([C:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH:37]=2)[O:26]1>C(Cl)(Cl)Cl.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:5]2[CH:6]=[N:7][C:2]([N:35]3[CH2:34][CH2:33][C:32]([B:27]4[O:28][C:29]([CH3:31])([CH3:30])[C:25]([CH3:38])([CH3:24])[O:26]4)=[CH:37][CH2:36]3)=[N:3][C:4]2=[O:16])=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 211054611,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 1178396204-chloro-1-(4-chlorobenzyl)-1,3,5-triazin-2(1H)-one

生成物 1

HCID 1232364521-(4-Chlorobenzyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2(1H)-one収率 40.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒2 回

実験手順

To a chloroform solution (3.0 mL) of 4-chloro-1-(4-chlorobenzyl)-1,3,5-triazin-2(1H)-one (128 mg, 0.500 mmol) synthesized in Reference Synthesis Example 11, triethylamine (70.0 μL, 0.500 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (156 mg, 0.750 mmol) were added and the resultant mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1) to obtain the title compound (86.0 mg, yield 40%).

後処理

  1. additionwere added
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1)

出典と根拠

ORDレコード
ord-b79a9bf4b730424e83799c832c62e776
出典データセット
uspto-grants-2016_08
特許番号
US09403798B2

反応ノート

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