N-Iodosuccinimide → HCID 66733407, compound

HRID 2047061Notes

Reaction equation

HRID 2047061 reaction equation
[CH3:1][Si:2]([CH3:38])([CH3:37])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[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][CH:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH:9]=1.[I:39]N1C(=O)CCC1=O>C(#N)C>[CH3:34][Si:33]([CH3:36])([CH3:35])[CH2:32][CH2:31][O:30][CH2:29][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:37])[CH3:38])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:39])=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66733619Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

Product 1

HCID 66733407HCID 66733407, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 50 mL roundbottom flask was charged ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (381 mg, 0.68 mmol) and acetonitrile (10 mL). To this solution was added N-Iodosuccinimide (167 mg, 0.74 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the crude oil was purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient) to yield ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (335 mg, 0.49 mmol, 72% yield) as clear oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude oil was purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-89ab681187c044a3bdc039121ffb7f27
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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