Sulfuric Acid → 5-(5-Acetyl-2-butoxy-3-pridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354191

反応式

HRID 354191 の反応式
S(=O)(=O)(O)[OH:2].[CH2:6]([O:10][C:11]1[C:16]([C:17]2[NH:18][C:19](=[O:33])[C:20]3[C:21](=[C:23]([CH2:31][CH3:32])[N:24]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[N:25]=3)[N:22]=2)=[CH:15][C:14]([C:34]#[CH:35])=[CH:13][N:12]=1)[CH2:7][CH2:8][CH3:9]>CC(C)=O.CO.S([O-])([O-])(=O)=O.[Hg+2]>[C:34]([C:14]1[CH:15]=[C:16]([C:17]2[NH:18][C:19](=[O:33])[C:20]3[C:21](=[C:23]([CH2:31][CH3:32])[N:24]([CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[N:25]=3)[N:22]=2)[C:11]([O:10][CH2:6][CH2:7][CH2:8][CH3:9])=[N:12][CH:13]=1)(=[O:2])[CH3:35]

参加物

6

反応物 2

HCID 1118Sulfuric AcidHCID 1356742315-(2-Butoxy-5-ethynyl-3-pyridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

生成物 1

HCID 1354447225-(5-Acetyl-2-butoxy-3-pridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

試薬・触媒・溶媒 3

HCID 24544Mercuric sulfate触媒HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

1 N Sulfuric acid (1 mL) was added to a stirred solution of 5-(2-butoxy-5-ethynyl-3-pyridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 46) (280 mg, 0.69 mmol) in acetone (8 mL) at room temperature. Mercury sulfate (40 mg, 0.14 mmol) was added and the mixture heated at reflux for 5 h. The reaction mixture was cooled, diluted with methanol (10 mL), filtered and the filtrate washed with further methanol. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (100 mL). The aqueous was washed with a further 100 mL of ethyl acetate and the combined organics dried (MgSO4) and concentrated. Purification by flash column chromatography (elution with 95% dichloromethane/methanol) gave the product as a cream coloured solid (140 mg).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washthe filtrate washed with further methanol
  6. customThe solvent was evaporated
  7. customthe residue partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (100 mL)
  8. washThe aqueous was washed with a further 100 mL of ethyl acetate
  9. dry with materialthe combined organics dried (MgSO4)
  10. concentrationconcentrated
  11. customPurification
  12. washby flash column chromatography (elution with 95% dichloromethane/methanol)
  13. customgave the product as a cream

出典と根拠

ORDレコード
ord-4a0161489eee48d1a7fb50cdbbb050c3
出典データセット
uspto-grants-2004_06
特許番号
US06756373B1

関連ノート

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