Imidazole → 9-(2,6-dimethylstyryl)-N-(4-(dimethylphosphoryl)phenyl)-2-(1H-imidazol-1-yl)-9H-purin-6-amine

HRID 2041926Notes

Reaction equation

HRID 2041926 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][C:9]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:10]=1/[CH:11]=[CH:12]/[N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16](Cl)=[N:17][C:18]=2[NH:22][C:23]1[CH:28]=[CH:27][C:26]([P:29]([CH3:32])([CH3:31])=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[CH3:8][C:9]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:10]=1/[CH:11]=[CH:12]/[N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[N:17][C:18]=2[NH:22][C:23]1[CH:28]=[CH:27][C:26]([P:29]([CH3:32])([CH3:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 86631262(E)-9-(2,6-dimethylstyryl)-2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine

Product 1

HCID 445618309-(2,6-dimethylstyryl)-N-(4-(dimethylphosphoryl)phenyl)-2-(1H-imidazol-1-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.16 g, 2.36 mmol) was dissolved in DMF (1.0 mL) in a CEM 10 mL microwave tube and to this was added NaH (0.09 g, 60% dispersion in mineral oil). The content was stirred at room temperature until no more bubbling was observed (˜10 min). Then (E)-9-(2,6-dimethylstyryl)-2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine (0.12 g, 0.236 mmol) was added. The reaction was heated with microwave (120° C., 10 min). Solvent was removed on rotavapor and the residue was partitioned between EtOAc/water, and the organic layer was separated and dried Na2SO4. The product was purified on ISCO combiFlash (12 g silica gel column, 5% MeOH/DCM): MS [M+H]+ 484.

Workup

  1. customno more bubbling
  2. custom(˜10 min)
  3. temperatureThe reaction was heated with microwave (120° C., 10 min)
  4. customSolvent was removed on rotavapor
  5. customthe residue was partitioned between EtOAc/water
  6. customthe organic layer was separated
  7. customThe product was purified on ISCO combiFlash (12 g silica gel column, 5% MeOH/DCM)

Sources & evidence

ORD record
ord-5b570a6e3fd2452cb0164f6137b9c43d
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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