2-Methoxyethylamine → 3-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(2-methoxyethylamino)pyridin-3-yl]-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

HRID 990243Notes

Reaction equation

HRID 990243 reaction equation
C(O[C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:22])[C:13]3[C:14](=[C:16]([CH2:20][CH3:21])[N:17]([CH3:19])[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:6][N:5]=1)C.[CH3:34][O:35][CH2:36][CH2:37][NH2:38]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:20]([C:16]1[N:17]([CH3:19])[N:18]=[C:13]2[C:12](=[O:22])[NH:11][C:10]([C:9]3[C:4]([NH:38][CH2:37][CH2:36][O:35][CH3:34])=[N:5][CH:6]=[C:7]([S:23]([N:26]4[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]4)(=[O:24])=[O:25])[CH:8]=3)=[N:15][C:14]=12)[CH3:21]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 1358163675-[2-Ethoxy-5-(4-ethylpiperazin-1-ylsulphonyl)pyridin-3-yl]-3-ethyl-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1358163773-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(2-methoxyethylamino)pyridin-3-yl]-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-oneYield 69%

Reagents, catalysts & solvents 1

HCID 24463Copper sulfate pentahydrateCatalyst

Procedure

A mixture of the title compound of Example 78 (200 mg, 0.42 mmol),and copper (II) sulphate pentahydrate (150 mg, 0.60 mmol) in 2-methoxyethylamine (2 ml) was heated under reflux for 2 hours, then cooled. The reaction was partitioned between dichloromethane (20 ml) and aqueous sodium carbonate solution (5 ml), and the layers separated. The organic phase was dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using an elution gradient of dichloromethane: methanol (98:2 to 95:5) to afford the title compound (150 mg, 69%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customThe reaction was partitioned between dichloromethane (20 ml) and aqueous sodium carbonate solution (5 ml)
  5. customthe layers separated
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using an elution gradient of dichloromethane: methanol (98:2 to 95:5)

Sources & evidence

ORD record
ord-ecfe5121877b4de7a1987909549c5fe0
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

Loading…