N-Iodosuccinimide → Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate

HRID 2047121Notes

Reaction equation

HRID 2047121 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[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[CH:9]=1.C1C(=O)N([I:46])C(=O)C1>CC#N>[CH3:36][Si:33]([CH3:35])([CH3:34])[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:46])=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67494768HCID 67494768, compound

Product 1

HCID 67494509Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate 3.95 g, 7.0 mmol) in CH3CN (30 mL) was added NIS (1.65 mg, 7.0 mmol). The mixture was stirred at rt for 2 h and diluted with EtOAC (50 mL) and washed with saturated sodium thiosulfate, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to the title compound as a light brown oil. LC/MS RT=2.49 min. Mass calculated for, M+H 689.23, observed 389.17.

Workup

  1. additiondiluted with EtOAC (50 mL)
  2. washwashed with saturated sodium thiosulfate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to the title compound as a light brown oil

Sources & evidence

ORD record
ord-0a798e50a76c4711be1f8863326e29b7
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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