Sodium Methoxide → HCID 15462516, compound

HRID 842065Notes

Reaction equation

HRID 842065 reaction equation
Cl[C:2]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH2:19][C:20]([N:22]([CH2:29][CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21])[C:5](=[O:18])[N:6]2[CH3:17].[CH3:31][O-:32].[Na+]>CO.CN1CCN(C)C1=O>[CH2:29]([N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](=[O:21])[CH2:19][N:4]1[C:3]2[C:7](=[N:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:2]=2[O:32][CH3:31])[N:6]([CH3:17])[C:5]1=[O:18])[CH3:30]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 15462515HCID 15462515, compound

Product 1

HCID 15462516HCID 15462516, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

A mixture of 6-chloro-N-ethyl-8,9-dihydro-9-methyl-8-oxo-2-phenyl-N-phenyl-7H-purin-7-acetamide (0.6 g) obtained in Example 45, a 28% solution of sodium methoxide in methanol (0.3 g), methanol (20 ml) and 1,3-dimethyl-2-imidazolidinone (5 ml) is refluxed for four hours. The reaction mixture is concentrated under reduced pressure, and to the residue are added water and chloroform. The chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from ethanol to give the desired compound (0.3 g).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionto the residue are added water and chloroform
  3. customThe chloroform layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cb3f1c5f389146ca9a02ffc27bc04d1b
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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