N-Iodosuccinimide → 4-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone

HRID 334359Notes

Reaction equation

HRID 334359 reaction equation
[CH3:1][Si:2]([CH3:33])([CH3:32])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH:9]=1.C1C(=O)N([I:41])C(=O)C1>CC#N>[CH3:29][Si:28]([CH3:31])([CH3:30])[CH2:27][CH2:26][O:25][CH2:24][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:33])([CH3:32])[CH3:1])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:41])=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 665836364-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone

Product 1

HCID 665836524-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanoneYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (775 mg, 1.58 mmol) in CH3CN (10 mL) was added NIS (391 mg, 1.74 mmol). The resulting solution was stirred at rt for 30 min before quenching with Na2S2O3 (sat.). CH3CN was removed under reduced pressure. The residue was diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-20% EtOAc/Hexanes, Rf=0.3 in 20% EtOAc) to afford 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone as a pale yellow oil (751 mg).

Workup

  1. custombefore quenching with Na2S2O3 (sat.)
  2. customCH3CN was removed under reduced pressure
  3. additionThe residue was diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by a SiO2 column (0-20% EtOAc/Hexanes, Rf=0.3 in 20% EtOAc)

Sources & evidence

ORD record
ord-8397b9c86d3049568baa06c8ba6aa846
Source dataset
uspto-grants-2014_11
Patent number
US08883801B2

Reaction notes

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