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Potassium Hydroxide → Allyl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1850673
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HRID 1850673 반응식
O1CCO[CH:2]1[CH2:6][C:7](=O)[C:8]([F:11])([F:10])[F:9].[NH2:13][C:14]1[C:18]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:17]([NH2:25])[NH:16][N:15]=1.[OH-].[K+]>O1CCOCC1>[NH2:25][C:17]1[C:18]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:14]2[N:13]=[C:7]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:2][N:15]2[N:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 552960491-(1,3-Dioxolane-2-yl)-3,3,3-trifluoropropane-2-oneHCID 73554792Allyl 3,5-diamino-1H-pyrazole-4-carboxylate

생성물 1

HCID 90417814Allyl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate수율 79%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

3-(1,3-Dioxolan-2-yl)-1,1,1-trifluoro-propan-2-one (55.58 g, 301.9 mmol) and allyl 3,5-diamino-1H-pyrazole-4-carboxylate (55 g, 301.9 mmol) were dissolved in 1,4-dioxane (330 mL). KOH (1.694 g, 30.19 mmol) was added and the yellow suspension was stirred at room temperature for 4 h30 min. The reaction mixture was heated at 90° C. for 16 h. The mixture was cooled down to room temperature. The reaction mixture was concentrated onto silica and purified by column chromatography (CombiFlash Companion XL, 1.5 kg column, 0.5 to 40% EtOAc in DCM) to afford allyl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 4d as a bright yellow solid (68 g, 79% yield).

후처리

  1. temperatureThe reaction mixture was heated at 90° C. for 16 h
  2. temperatureThe mixture was cooled down to room temperature
  3. concentrationThe reaction mixture was concentrated onto silica
  4. custompurified by column chromatography (CombiFlash Companion XL, 1.5 kg column, 0.5 to 40% EtOAc in DCM)

출처 및 근거

ORD 기록
ord-e981510f0ee84801ad9bbeebee7ef5cc
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957078B2

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