Trimethylsilyl iodide → HCID 23434639, compound

HRID 270731Notes

Reaction equation

HRID 270731 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[O:4][C:5]1[C:26](=[O:27])[N:25]([CH3:28])[C:8]2[N:9]=[C:10]([NH:13][CH:14]3[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]3)[N:11]=[CH:12][C:7]=2[CH:6]=1.I[Si](C)(C)C>ClCCl.CO>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[O:4][C:5]1[C:26](=[O:27])[N:25]([CH3:28])[C:8]2[N:9]=[C:10]([NH:13][CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[N:11]=[CH:12][C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 23434656HCID 23434656, compound

Product 1

HCID 23434639HCID 23434639, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the free base of ethyl 4-{[6-(2-fluorophenoxy)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}piperidine-1-carboxylate (0.500 g, 1.13 mmol) and iodotrimethylsilane (0.32 mL, 2.27 mmol) in 5 mL dichloromethane was refluxed. After 4 hours, additional iodotrimethylsilane (0.32 mL, 2.27 mmol) was added and the reaction stirred at room temperature for 3 days. The reaction was diluted with methanol and evaporated, with the residue taken up in a methanolic solution of sodium methoxide (0.5 M, 9.1 mL) and re-evaporated.

Workup

  1. temperaturewas refluxed
  2. customevaporated, with the residue
  3. customre-evaporated

Sources & evidence

ORD record
ord-7ece39bdeb6249d293619b23f8c494d9
Source dataset
uspto-grants-2008_11
Patent number
US07449581B2

Reaction notes

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