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

HRID 1581938Notes

Reaction equation

HRID 1581938 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-b070af7f301f4f91b7bf305e0bfdb971
Source dataset
uspto-grants-2004_05
Patent number
US06734183B2

Reaction notes

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