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

HRID 1398868ノート

反応式

HRID 1398868 の反応式
[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

参加物

5

反応物 2

HCID 130809804-Chloro-2-methoxy-6-methyl-5-nitropyrimidineHCID 178477797HCID 178477797、化合物

生成物 1

HCID 687373032-Methoxy-4,6-dimethyl-5-nitropyrimidine収率 93.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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 (2.20 g, 1.90 mmol) in tetrahydrofuran (60 mL) at 0° C., 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 (3-0.37 g, 18.4 mmol, 93%).

後処理

  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

出典と根拠

ORDレコード
ord-bcf564f0e4554ae1907b8567aef0f6e4
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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