2,4-Dichloro-6-methyl-5-nitropyrimidine → 4-Chloro-2-methoxy-6-methyl-5-nitropyrimidine

HRID 1398867노트

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HRID 1398867 반응식
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([Cl:11])[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([CH3:15])[N:6]=1>CO.O>[Cl:11][C:9]1[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([CH3:15])[N:6]=[C:5]([O:2][CH3:1])[N:10]=1

참가 물질

5

반응물 2

HCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 10942334Sodium Methoxide

생성물 1

HCID 130809804-Chloro-2-methoxy-6-methyl-5-nitropyrimidine수율 25.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

Sodium methoxide (28% solution in methanol, 47.0 g, 244 mmol) was added dropwise to a stirred solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (48.3 g, 232 mmol) in methanol (600 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. The mixture was diluted with water, concentrated, 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 0-15% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (11.9 g, 58.5 mmol, 25%).

후처리

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-b2e50060e1244ab59c44ff4aec67228a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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