Acetic Acid → HCID 178469952, 화합물

HRID 1631293노트

반응식

HRID 1631293 반응식
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.C([O:14]/[CH:15]=[CH:16]/[C:17](OCC)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].CC(O)=O>CN(C=O)C>[OH:14][C:15]1[CH:16]=[CH:17][N:3]2[N:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 5366269Ethyl (2E)-3-ethoxy-2-propenoateHCID 178469928HCID 178469928, 화합물

생성물 1

HCID 178469952HCID 178469952, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

Ethyl 3-amino-1H-pyrazole-4-carboxylate (25.0 g, 161 mmol) and (E)-ethyl 3-ethoxyacrylate (35.8 ml, 242 mmol) were mixed in DMF (537 mL). Cesium carbonate (78.7 g, 242 mmol) was added and the mixture heated to 110° C. for 15 hours. The reaction mixture was cooled to ambient temperature and acidified with HOAc to pH 4. The resultant precipitate was filtered and washed with water and EtOAc, yielding the title compound as a fluffy white solid. Additional material was obtained by an aqueous workup. The filtrate was concentrated to remove the DMF, was diluted in EtOAc (500 mL) and washed with H2O. The resultant precipitate in the EtOAc layer was filtered and washed with water and EtOAc to obtain additional product. The solids were pooled and dried in vacuum to afford ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (33.3 g, 100% yield) as a fluffy white solid. MS (apci) m/z=206.2 (M−H).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationThe resultant precipitate was filtered
  3. washwashed with water and EtOAc

출처 및 근거

ORD 기록
ord-da5a9895b2e947db98d5157375bcce44
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791123B2

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