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Chlorotrimethylsilane → 2-(5-[4-(4-Bromophenyl)piperazino]sulfonylpent-4-enyl)pyrimidine

HRID 1581938
ノート
印刷プレビュー

反応式

HRID 1581938 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[N:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[CH2:39][CH2:40][CH2:41][CH:42]=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH:17]=[CH:42][CH2:41][CH2:40][CH2:39][C:34]3[N:35]=[CH:36][CH:37]=[CH:38][N:33]=3)(=[O:15])=[O:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium hexamethyldisilazaneHCID 115283684-(Pyrimidin-2-yl)butanalHCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

生成物 1

HCID 695961252-(5-[4-(4-Bromophenyl)piperazino]sulfonylpent-4-enyl)pyrimidine

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-20 °C

実験手順

To the 1-(4-bromophenyl)-4-(methanesulfonyl)piperazine (902 mg, 2.0 mmol) suspended in anhydrous THF (15 ml), under Nitrogen, cooled to between −20 and −30° C. was added sequentially Lithium bis(trimethylsilyl)amide (1.0 M in THF, 4.0 ml), Chlorotrimethylsilane (217 mg, 2.0 mmol, 253 μl) and 4-pyrimidin-2-ylbutanal (300 mg, 2.0 mmol). The mixture was stirred at −20° C. for 1 hour, quenched with saturated ammonium chloride solution and allowed to stand at ambient temperature overnight. The solvents were removed in vacuo and the residue partitioned between dichloromethane (15 ml) and water (5 ml), the organics separated and chromatogrammed (50 g Silica Bond Elute, eluted with 0→100% Ethyl Acetate/Hexane gradient) to give the 2-(5-[4-(4-bromophenyl)piperazino]sulfonylpent-4-enyl)pyrimidine as a white crystalline material (759 mg, 84% Yield)

後処理

  1. temperaturecooled to between −20 and −30° C.
  2. customquenched with saturated ammonium chloride solution
  3. waitto stand at ambient temperature overnight
  4. customThe solvents were removed in vacuo
  5. customthe residue partitioned between dichloromethane (15 ml) and water (5 ml)
  6. customthe organics separated
  7. wash(50 g Silica Bond Elute, eluted with 0→100% Ethyl Acetate/Hexane gradient)

出典と根拠

ORDレコード
ord-b070af7f301f4f91b7bf305e0bfdb971
出典データセット
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06734183B2

反応ノート

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