1-(2-Pyrimidinyl)piperazine → HCID 9933274, compound

HRID 852174Notes

Reaction equation

HRID 852174 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]3[CH2:14][O:13]3)=[CH:8][CH:7]=2)[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[N:21]1([C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(O)C>[S:1]1[CH:5]=[C:4]([C:6]2[CH:16]=[CH:15][C:9]([O:10][CH2:11][C@H:12]([OH:13])[CH2:14][N:24]3[CH2:25][CH2:26][N:21]([C:27]4[N:28]=[CH:29][CH:30]=[CH:31][N:32]=4)[CH2:22][CH2:23]3)=[CH:8][CH:7]=2)[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

4

Reactant 2

HCID 887471-(2-Pyrimidinyl)piperazineHCID 17906295HCID 17906295, compound

Product 1

HCID 9933274HCID 9933274, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Combine 2-(4-benzo[b]thiophen-3-yl-phenoxymethyl)-oxirane (200 mg, 0.708 mmol), 2-piperazin-1-yl-pyrimidine (465 mg, 2.83 mmol) and ethanol (4 mL). Apply heat (75° C.) to the homogeneous reaction mixtures and stir for 6 hours. Concentrate (in vacuo) and purify by column chromatography using a Waters Sep-Pak silica gel cartridge (10 g) and elution with graded solvent mixtures from 50% ethyl acetate in heptane to 100% ethyl acetate. Concentrate the appropriate fractions, dissolve in dichloromethane and re-evaporate under a stream of nitrogen. Dry the sample using medium heat and reduced pressure to give the title compound as a clear oil (0.285 mg, 90% Yield). Purity by LC/MS=99%, [M+H]+=447.

Workup

  1. customto the homogeneous reaction mixtures
  2. concentrationConcentrate (in vacuo)
  3. custompurify by column chromatography
  4. washa Waters Sep-Pak silica gel cartridge (10 g) and elution with graded solvent mixtures from 50% ethyl acetate in heptane to 100% ethyl acetate
  5. concentrationConcentrate the appropriate fractions
  6. dissolutiondissolve in dichloromethane
  7. customre-evaporate under a stream of nitrogen
  8. customDry the sample
  9. temperatureusing medium heat

Sources & evidence

ORD record
ord-8979414396e54191ae3458fb99440e29
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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