N-Iodosuccinimide → HCID 71239649, compound

HRID 1403227Notes

Reaction equation

HRID 1403227 reaction equation
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[CH3:36])=[C:18]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:17]=2)[CH:13]=[CH:12][N:11]=1>CN(C=O)C>[NH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[CH3:36])=[C:18]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:17]=2)[C:13]([I:1])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 71239587HCID 71239587, compound

Product 1

HCID 71239649HCID 71239649, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-iodosuccinimide (356 mg, 1.58 mmol) was added to a solution of ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate (700 mg, 1.44 mmol) in DMF (15 mL). The reaction mixture was heated at 60° C. for 4 h, allowed to cool to room temperature, concentrated and then diluted with EtOAc (30 mL). The organic phase was washed with sodium sulfite, water, brine, dried over sodium sulphate, and evaporated to afford the title compound as yellow solid (0.70 g, 79%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. additiondiluted with EtOAc (30 mL)
  4. washThe organic phase was washed with sodium sulfite, water, brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-6ae226ac03eb4afdbd5dc383e3ef051a
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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