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

HRID 1244436
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HRID 1244436 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-20 °C

실험 절차

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 (1.0M 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)

후처리

  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)

출처 및 근거

ORD 기록
ord-e7da8d52331343f7b2418d609f90fa29
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122551B2

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