Acetonitrile → ethyl 1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate

HRID 539891

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HRID 539891 반응식
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[N:24]=C(Cl)[C:22]([F:26])=[CH:21][N:20]=1.C(#[N:29])C>C(OCC)(=O)C>[Cl:18][C:19]1[N:24]=[C:3]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:1])=[N:29]2)[C:22]([F:26])=[CH:21][N:20]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylateHCID 2507052,4-Dichloro-5-fluoropyrimidine

생성물 1

HCID 86659253ethyl 1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate수율 85%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of ethyl 3-methyl-1H-pyrrole-4-carboxylate (3.15 g, 20.5 mmol) in acetonitrile (MeCN) were added potassium carbonate (5.7 g, 41 mmol) and 2,4-dichloro-5-fluoropyrimidine (3.4 g, 20.5 mmol) at room temperature. The resulting slurry was heated at 80° C. for 3 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). It was diluted with ethyl acetate and washed with brine. The collected organic layer was dried over anhydrous sodium sulfate and then partially concentrated in vacuo. To this, n-hexanes were added to form pale yellow precipitates. The resulting solids were collected by filtration and rinsed with n-hexanes and then dried under high vacuum to give 4.9 g (85%) of the target intermediate 3; MS (ESI) m/z 285 [M+H]+

후처리

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. washwashed with brine
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. concentrationpartially concentrated in vacuo
  5. additionTo this, n-hexanes were added
  6. customto form pale yellow precipitates
  7. filtrationThe resulting solids were collected by filtration
  8. washrinsed with n-hexanes
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-2857bc4ecf8a41a8893758f890bd6447
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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