Hydrochloric Acid → Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

HRID 965998

反応式

HRID 965998 の反応式
Cl.[C:2]1([CH3:17])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[C:11]([CH3:16])=[N:12][NH:13][C:14]=1[NH2:15].[C:18]([C:20](=[C:26](OCC)[CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]>CO>[NH2:19][C:18]1[N:13]2[N:12]=[C:11]([CH3:16])[C:10]([C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:17])=[C:14]2[N:15]=[C:26]([CH3:27])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 178424562HCID 178424562、化合物

生成物 1

HCID 22249773Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate収率 20.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Concentrated hydrochloric acid (0.1 mL) was added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (2.5 g, 11.61 mmol) and ethyl 2-cyano-3-ethoxy-2-butenoate (2.13 g, 11.61 mmol) in methanol (30 mL), followed by heating under reflux for 18 hours. The reaction mixture was evaporated as it was. Then, water was added and a 5N aqueous solution of sodium hydroxide was added under ice-cooling, to neutralize. Further, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane), to give the title compound (835 mg).

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was evaporated as it
  4. additionThen, water was added
  5. additiona 5N aqueous solution of sodium hydroxide was added under ice-
  6. temperaturecooling
  7. extractionFurther, the mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-af8f0395d22b46a497e7bff9652ebe72
出典データセット
uspto-grants-2005_10
特許番号
US06951865B2

関連ノート

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