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

HRID 705030ノート

反応式

HRID 705030 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dfc4eb85dce447bd8e6e7a141bc442cd
出典データセット
uspto-grants-2015_11
特許番号
US09173396B2

反応ノート

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