N-Iodosuccinimide → Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate

HRID 2047049Notes

Reaction equation

HRID 2047049 reaction equation
[CH3:1][Si:2]([CH3:37])([CH3:36])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)[CH:9]=1.C1C(=O)N([I:45])C(=O)C1>C(#N)C>[CH3:33][Si:32]([CH3:35])([CH3:34])[CH2:31][CH2:30][O:29][CH2:28][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:36])([CH3:1])[CH3:37])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:45])=[C:12]2[N:11]=[C:10]([O:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66737940Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate

Product 1

HCID 66733924Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yloxy)benzoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate (450 mg, 0.81 mmol) was dissolved in ACN (15 mL) and NIS (200 mg, 0.88 mmol) was added. The resulting mixture was stirred at room temperature for 2 h and then the solvent was removed under reduced pressure. The residue was purified with column (silica gel, 10% EtOAc/Hexane) gave the product, methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yloxy)benzoate (541 mg) as yellowish oil. HPLC-MS tR=3.10 min (UV254 nm); mass calculated for formula C26H39IN4O5Si2 670.2, observed LCMS m/z 671.2 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified with column (silica gel, 10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-c3ac8cc99eae462cbccc2019a74f9fc2
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…