4,6-Dichloro-5-nitropyrimidine → 4-chloro-6-methoxy-5-nitropyrimidine

HRID 1723677ノート

反応式

HRID 1723677 の反応式
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9](Cl)[N:8]=[CH:7][N:6]=1>CO>[Cl:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:2][CH3:1])[N:8]=[CH:7][N:6]=1

参加物

4

反応物 2

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 10942334Sodium Methoxide

生成物 1

HCID 2522044-chloro-6-methoxy-5-nitropyrimidine収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

Sodium methoxide (2.70 g, 50.0 mmol) was added portionwise over 10 min to a 0° C. suspension of 4,6-dichloro-5-nitropyrimidine (4.85 g, 25.0 mmol) in methanol (90 ml). On complete addition the mixture was stirred at 0° C for 2 h. The precipitate was filtered and the filtrate evaporated. The residue was suspended in isohexane and filtered. The filtrate was evaporated and the residue purified by flash column chromatography on silica, eluting with 5% ethyl acetate in isohexane. Collecting appropriate fractions gave 4-chloro-6-methoxy-5-nitropyrimidine (3.50 g, 74%) as a white solid: δH (400 MHz, CDCl3) 4.15 (3H, s), 8.65 (1H, s).

後処理

  1. additionOn complete addition the mixture
  2. filtrationThe precipitate was filtered
  3. customthe filtrate evaporated
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash column chromatography on silica
  7. washeluting with 5% ethyl acetate in isohexane
  8. customCollecting appropriate fractions

出典と根拠

ORDレコード
ord-07e7aec29ab64322bb7090cab3ebf0c3
出典データセット
uspto-grants-2009_02
特許番号
US07485640B2

反応ノート

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