N-Iodosuccinimide → 1-cyclohexyl-3-[7-iodo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 906006Notes

Reaction equation

HRID 906006 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([I:35])C(=O)C1>CC(C)=O>[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([I:35])=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 673858151-cyclohexyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 673859971-cyclohexyl-3-[7-iodo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 1-Cyclohexyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (2.67 g) and NIS (742 mg, 3.30 mmol) in 12 mL of acetone was stirred at RT for 4 hr, filtered, and washed with small amount of acetone. The solid was dried under high vacuum to give 701 mg of 1-cyclohexyl-3-[7-iodo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as an off-white solid (45% yield for 2 steps).

Workup

  1. filtrationfiltered
  2. washwashed with small amount of acetone
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-963f38c86e03413cbd326fdcb2a1dfdc
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

Loading…