Sodium Hydroxide → 6-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 42606

反応式

HRID 42606 の反応式
N[C:2]1[C:10]2[C:5](=[N:6][C:7]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[CH:9]=2)[NH:4][N:3]=1.N([O-])=O.[Na+].O[PH2]=O.[OH-].[Na+]>CC(O)=O.O.Cl>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:7]2[N:6]=[C:5]3[NH:4][N:3]=[CH:2][C:10]3=[CH:9][C:8]=2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[CH:20][CH:21]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 178503413HCID 178503413、化合物

生成物 1

HCID 670146776-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine収率 42%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 3-amino-6-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine (10.00 g, 28.4 mmol, obtained in example 180) in AcOH (52 mL), water (22 mL) and HCl conc. (5.7 mL), cooled to 0° C., a solution of NaNO2 (2.30 g, 33.4 mmol) in water (7.5 mL) was added dropwise. It was stirred for 30 min at 0° C., and H3PO2 (50% aqueous solution, 56.8 mL) was added slowly. It was stirred at 0° C. for 6 h. It was allowed to cool to room temperature, basified at 0° C. by slow addition of 6 N NaOH hasta pH=8 and was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 4.00 g of the title compound (yield: 42%)

後処理

  1. stirringIt was stirred at 0° C. for 6 h
  2. temperatureto cool to room temperature
  3. extractionwas extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained
  7. customwas purified by chromatography on silica gel
  8. temperatureof increasing polarity as eluent

出典と根拠

ORDレコード
ord-36bc6544a1ae40ee983059e6b2d908c5
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

関連ノート

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