Potassium Carbonate → 2-{6-[4-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine

HRID 705030노트

반응식

HRID 705030 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.Br[C:13]1[N:18]=[C:17]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]2[CH:5]=[N:1][N:2]([C:13]3[N:18]=[C:17]([C:19]4[N:20]=[CH:21][CH:22]=[CH:23][N:24]=4)[CH:16]=[CH:15][CH:14]=3)[CH:3]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 14179073-(1H-pyrazol-4-yl)pyridineHCID 158812582-(6-Bromopyridin-2-yl)pyrimidine

생성물 1

HCID 675167362-{6-[4-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

DMF was added to 0.8 g (5.5 mmol) of 3-(1H-pyrazol-4-yl)pyridine (Angew. Chemie, 2006, 118 (8) 1304), 1.3 g (5.5 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine (WO 2010/006713), 0.29 g (0.82 mmol) of copper-8-hydroxyquinoline complex (cf. Tetrahedron Lett, 2006, 149) and 2.28 g (16.5 mmol) of potassium carbonate, and the mixture was stirred at 120° C. under argon for 16 hours. The entire reaction mixture was then concentrated under reduced pressure. The residue was admixed with aqueous citric acid, aqueous sodium chloride, ethyl acetate and diluted aqueous sodium hydroxide solution until the mixture gave an alkaline reaction (pH=9), the mixture was extracted four times with ethyl acetate and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/acetone). This gave 0.56 g (32% of theory) of 2-{6-[4-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine.

후처리

  1. customThe entire reaction mixture
  2. concentrationwas then concentrated under reduced pressure
  3. customgave
  4. customan alkaline reaction (pH=9)
  5. extractionthe mixture was extracted four times with ethyl acetate
  6. dry with materialthe combined organic phases were dried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (mobile phase: cyclohexane/acetone)

출처 및 근거

ORD 기록
ord-dfc4eb85dce447bd8e6e7a141bc442cd
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173396B2

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