Malonic Acid → (E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine

HRID 440717

反応式

HRID 440717 の反応式
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].N1CCCCC1.C([C:16]1[C:17]([O:24][CH3:25])=[N:18][C:19]([O:22][CH3:23])=[N:20][CH:21]=1)=O>N1C=CC=CC=1>[C:3](/[CH:2]=[CH:1]/[C:16]1[C:17]([O:24][CH3:25])=[N:18][C:19]([O:22][CH3:23])=[N:20][CH:21]=1)([OH:5])=[O:4]

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 5977822,4-Dimethoxypyrimidine-5-carbaldehyde

生成物 1

HCID 688432(E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Malonic acid (13.03 g; 126.2 mmol) and redistilled piperidine (2 ml) were added to a solution of 5-formyl-2,4,dimethoxypyrimidine (10.52 g; 6.2.6 mmol) in dry pyridine (60 ml). The mixture was heated on a steam bath for 10 h then the solvent was removed by distillation under reduced pressure. The residual oil was re-evaporated from water (3×25 ml) and the solid thus obtained recrystallised firstly from water and then from dry methanol to give the product as white needles, yield 6.45 g; a second crop was obtained from the filtrate (1.08 g). Total yield 7.53g (57%). Mass spectrum: (El) m/z 210 (M+). Analysis, found: C,52.1;H,4.8;N, 13.1%: C9H10N2O4 requires: C, 52.43; H, 4.79; N, 13.33%.

後処理

  1. temperatureThe mixture was heated on a steam bath for 10 h
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residual oil was re-evaporated from water (3×25 ml)
  4. customthe solid thus obtained
  5. customrecrystallised firstly from water

出典と根拠

ORDレコード
ord-bfe7a1e8735440c4a77f68e7bd649b56
出典データセット
uspto-grants-1996_05
特許番号
US05521163

関連ノート

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