Ethyl 2-cyano-3-ethoxy-2-butenoate → Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

HRID 584790

반응식

HRID 584790 반응식
[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[C:10]([CH3:15])=[N:11][NH:12][C:13]=1[NH2:14].[C:17]([C:19](=[C:25](OCC)[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18]>C(O)C>[NH2:18][C:17]1[N:12]2[N:11]=[C:10]([CH3:15])[C:9]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:16])=[C:13]2[N:14]=[C:25]([CH3:26])[C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

참가 물질

4

반응물 2

HCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 178424562HCID 178424562, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Concentrated dihydrochloric 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 ethanol (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c3f82b1e7d644935a2658f6cfdf1868e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927221B2

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