Pyridine → 1H-Purine-2,6-dione, 3,7-dihydro-7-(2-chlorophenyl)-1,3-dimethyl-

HRID 1792028Notes

Reaction equation

HRID 1792028 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.N1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 2153TheophyllineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 30557701H-Purine-2,6-dione, 3,7-dihydro-7-(2-chlorophenyl)-1,3-dimethyl-Yield 17.9%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Theophylline (510 mg), 2-chlorophenyl boronic acid (1 g), and copper (II) acetate (220 mg) were suspended in N,N-dimethylformamide (10 ml), and pyridine (1 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 30% aqueous ammonia. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with ether to give 147 mg of the title compound.

Workup

  1. washwashed with 30% aqueous ammonia
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-a5fdccb69a534845ac96f83401c57e39
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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