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Hydrogen Peroxide → 1-Methyl-5-(2-propoxyphenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

HRID 862898
ノート
印刷プレビュー

反応式

HRID 862898 の反応式
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][CH2:20][CH3:21])[C:4]([CH2:23][CH2:24][CH3:25])=[N:3]1.OO.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[CH3:1][N:2]1[C:6]2[C:7](=[O:8])[NH:9][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][CH2:20][CH3:21])=[N:10][C:5]=2[C:4]([CH2:23][CH2:24][CH3:25])=[N:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 113937971-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 1357385471-Methyl-5-(2-propoxyphenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one収率 59%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide (0.34 g, 0.99 mmol) was added to a stirred mixture of 30% hydrogen peroxide solution (1.0 ml), potassium carbonate (0.54 g, 3.92 mmol), water (10 ml) and ethanol (5 ml). The mixture was heated under reflux for 38 hours and then evaporated under vacuum. The residue was suspended in water (20 ml), then the mixture acidified with 2N hydrochloric acid and extracted with dichloromethane (3×20 ml). The extracts were combined, dried (Na2SO4) and evaporated under vacuum. The resulting residue was chromatographed on silica gel (6 g), using a methanol in dichloromethane elution gradient (0.0-1.0%), to give an oil, successive trituration of which with ether gave the required product as a white solid (0.19 g, 59%), m.p. 111°-114° C. Found: C,66.26; H,6.92; N,17.15. C18 H22N4O2 requires C,66.23; H, 6.80; N, 17.17%.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 38 hours
  3. customevaporated under vacuum
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum
  7. customThe resulting residue was chromatographed on silica gel (6 g)
  8. washa methanol in dichloromethane elution gradient (0.0-1.0%)
  9. customto give an oil, successive trituration of which with ether

出典と根拠

ORDレコード
ord-142f9c2fdec4453a80b7e3c3f4415ab9
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05719283

反応ノート

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