N-Iodosuccinimide → 3-iodo-5-(4-(methylthio)phenoxy)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047039Notes

Reaction equation

HRID 2047039 reaction equation
[CH3:1][S:2][C:3]1[CH:35]=[CH:34][C:6]([O:7][C:8]2[CH:13]=[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:11]3[N:31]=[CH:32][CH:33]=[C:10]3[N:9]=2)=[CH:5][CH:4]=1.C1C(=O)N([I:43])C(=O)C1>C(#N)C>[I:43][C:33]1[CH:32]=[N:31][N:11]2[C:12]([N:14]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])=[CH:13][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:35][CH:34]=3)=[N:9][C:10]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667339295-(4-(methylthio)phenoxy)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 667354123-iodo-5-(4-(methylthio)phenoxy)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(4-(methylthio)phenoxy)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (490 mg, 0.81 m) 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, 3-iodo-5-(4-(methylthio)phenoxy)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (541 mg) as yellowish oil. HPLC-MS tR=3.18 min (UV254 nm); mass calculated for formula C25H39IN4O3SSi2 658.1, observed LCMS m/z 659.2 (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-4ba03f652ef34be286441e2017f17e08
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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