Potassium Carbonate → ethyl 1-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate

HRID 539893노트

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HRID 539893 반응식
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[N:24]=[C:23](Cl)[C:22]([CH3:26])=[CH:21][N:20]=1>C(#N)C>[Cl:18][C:19]1[N:24]=[C:23]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:1])=[N:3]2)[C:22]([CH3:26])=[CH:21][N:20]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 178469911HCID 178469911, 화합물

생성물 1

HCID 86698983ethyl 1-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate수율 61%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a solution of ethyl 3-methyl-1H-pyrazole-4-carboxylate (4.7 g, 30.6 mmol) in acetonitrile were added potassium carbonate (10.6 g, 75.0 mmol) and 2,4-dichloro-5-methylpyrimidine (5.0 g, 30.6 mmol) at room temperature. The resulting suspension was heated at 80° C. for 3 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). Volatiles were partially removed and the residue was extracted with ethyl acetate. The collected organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was recrystallized in a mixture of heptanes and ethyl acetate to afford the desired intermediate 5 as a pale yellow solid (5.2 g, 61%); MS (ESI) m/z 281 [M+H]+.

후처리

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. customVolatiles were partially removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe collected organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized in a mixture of heptanes and ethyl acetate

출처 및 근거

ORD 기록
ord-a7e2341da63d4c7697e27c97ea4f45a8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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