Adenine → HCID 178463004, compound

HRID 1725537Notes

Reaction equation

HRID 1725537 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].[N:22]1[C:30](N)=[C:29]2[C:25]([N:26]=[CH:27][NH:28]2)=[N:24][CH:23]=1>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:30]1[N:22]=[CH:23][N:24]=[C:25]2[C:29]=1[N:28]=[CH:27][NH:26]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 190AdenineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 178463004HCID 178463004, compoundYield 1.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 250 mg (0.870 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (12 mL), adenine (235 mg, 1.740 mmol) was added. The resulting mixture was stirred and refluxed during two days. The solvent was evaporated and the residue purified by column chromatography (silica gel, dichloromethane/methanol 95:5) and preparative HPLC/MS to yield the title compound (4.4 mg, 1.4% yield).

Workup

  1. temperaturerefluxed during two days
  2. customThe solvent was evaporated
  3. customthe residue purified by column chromatography (silica gel, dichloromethane/methanol 95:5) and preparative HPLC/MS

Sources & evidence

ORD record
ord-98dcc621632e49f588badd4a47834729
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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