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

HRID 1628510ノート

反応式

HRID 1628510 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 130809804-Chloro-2-methoxy-6-methyl-5-nitropyrimidine収率 25.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7b69c8a6b1714a279c2f60fe8ea8d0ac
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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