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

HRID 42606

반응식

HRID 42606 반응식
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

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 178503413HCID 178503413, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-36bc6544a1ae40ee983059e6b2d908c5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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