4-Chloro-2-methoxy-6-methyl-5-nitropyrimidine → 2-Methoxy-4,6-dimethyl-5-nitropyrimidine

HRID 1628511노트

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HRID 1628511 반응식
[Cl-].[CH3:2][Zn+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([CH3:14])[N:8]=[C:7]([O:15][CH3:16])[N:6]=1>O1CCCC1.O>[CH3:16][O:15][C:7]1[N:8]=[C:9]([CH3:14])[C:10]([N+:11]([O-:13])=[O:12])=[C:5]([CH3:2])[N:6]=1

참가 물질

5

반응물 2

HCID 130809804-Chloro-2-methoxy-6-methyl-5-nitropyrimidineHCID 178477797HCID 178477797, 화합물

생성물 1

HCID 687373032-Methoxy-4,6-dimethyl-5-nitropyrimidine수율 93.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Methylzinc chloride (2.0 M solution in tetrahydrofuran, 14.8 mL, 29.6 mmol) was added dropwise to a solution of 4-chloro-2-methoxy-6-methyl-5-nitropyrimidine (4.01 g, 19.7 mmol) and tetrakis(triphenyl phosphine)palladium (1.90 mmol) in tetrahydrofuran (60 mL), and the mixture was stirred at 50° C. for 50 minutes. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a pale yellow solid (3.37 g, 18.4 mmol, 93%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-2b625742042941e7bada9ce7bf46a03a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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