N-Iodosuccinimide → [1-(3-Iodo-imidazo[1,2-a]pyrimidin-2-yl)-ethyl]-carbamic acid benzyl ester

HRID 2036639Notes

Reaction equation

HRID 2036639 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]2[CH:21]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:30])C(=O)C1>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]2[C:21]=1[I:30])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 67432417(1-Imidazo[1,2-a]pyrimidin-2-yl-ethyl)-carbamic acid benzyl ester

Product 1

HCID 67432510[1-(3-Iodo-imidazo[1,2-a]pyrimidin-2-yl)-ethyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (1-imidazo[1,2-a]pyrimidin-2-yl-ethyl)-carbamic acid benzyl ester (5.3 g, 17.90 mmol) in acetonitrile (30 mL) was added n-iodosuccinimide (4.0 g, 17.90 mmol) and stirred at rt overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-4% MeOH in DCM to provide [1-(3-iodo-imidazo[1,2-a]pyrimidin-2-yl)-ethyl]-carbamic acid benzyl ester: LC-MS (ESI) m/z 422.8 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-90408c0f11ea43f7b6604540054b2623
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…