Potassium Carbonate → HCID 178508582, compound

HRID 1507884Notes

Reaction equation

HRID 1507884 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:8]2)=[C:4]([N:18]2[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][C:38](Cl)=[O:39])=[CH:34][CH:33]=1>O1CCOCC1.CO.O1CCOCC1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[NH:8]2)=[C:4]([N:18]2[CH2:24][CH2:23][CH2:22][N:21]([C:38](=[O:39])[CH2:37][O:36][C:35]3[CH:41]=[CH:42][C:32]([Cl:31])=[CH:33][CH:34]=3)[CH2:20][CH2:19]2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77771p-Chlorophenoxyacetyl chlorideHCID 178508581HCID 178508581, compound

Product 1

HCID 178508582HCID 178508582, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21966525Dioxane MethanolSolvent

Procedure

To a solution of 2-amino-6-(homopiperazin-1-yl)-8-(4-fluorophenyl)-9H-purine (0.2 mmol) in dioxane/methanol (1:1; 5 ml) was added potassium carbonate (55 mg, 0.4 mmol) and a solution of 4-chlorophenoxyacetyl chloride (60 mg, 0.24 mmol) in dioxane (1 ml). The resulting mixture was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was purified by flash chromatography on silica (methanol/dichloromethane 1:40), yielding the pure title compound (60 mg, 60%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by flash chromatography on silica (methanol/dichloromethane 1:40)

Sources & evidence

ORD record
ord-3634f06d77d84913bd65e8af4d5b2c37
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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