Diisopropylethylamine → 2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine

HRID 2041923Notes

Reaction equation

HRID 2041923 reaction equation
ClC1N=C2C(NC=N2)=C(Cl)N=1.C(N1C=NC2C1=NC=NC=2)=C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([P:30](=[O:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.[Cl:43][C:44]1[N:52]=[C:51]2[C:47]([N:48]=[CH:49][N:50]2[CH:53]=[CH2:54])=[C:46](Cl)[N:45]=1>CCO>[Cl:43][C:44]1[N:52]=[C:51]2[C:47]([N:48]=[CH:49][N:50]2[CH:53]=[CH2:54])=[C:46]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([P:30]([CH3:31])([CH3:32])=[O:33])=[CH:28][CH:29]=2)[N:45]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 206345534-(Dimethylphosphoryl)anilineHCID 57742405HCID 57742405, compoundHCID 866312612,6-Dichloropurine 9-vinyl purine

Product 1

HCID 866312602-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a sealed tube were added 2,6-dichloropurine-9-vinyl purine (0.43 g, 2 mmol), 4-aminophenyl-dimethylphosphine oxide (0.37 g, 2.2 mmol), and the solids were dissolved in ˜15 mL anhydrous EtOH under Ar. Then DIEA (1.0 mL, 6 mmol) was added. The reaction was heated at 105° C. for 3 overnights until the starting material 2,6-dichloro-9-vinylpurine had disappeared. Volatiles were removed by rotavaporing and the residue was partitioned between EtOAc/water. The organic layer was washed with water once more and dried over Na2SO4. The final product was purified by silica gel column chromatography (4˜8% MeOH/DCM).

Workup

  1. customVolatiles were removed
  2. customthe residue was partitioned between EtOAc/water
  3. washThe organic layer was washed with water once more
  4. dry with materialdried over Na2SO4
  5. customThe final product was purified by silica gel column chromatography (4˜8% MeOH/DCM)

Sources & evidence

ORD record
ord-6e59d39b077f4e9c92f731a523461499
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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