Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate → 5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one

HRID 903363

反応式

HRID 903363 の反応式
[CH:1]([CH:3]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[C:4](OCC)=O)=[O:2].C[O-].[Na+].[N+:20]([NH:23][C:24]([NH2:26])=[NH:25])([O-:22])=[O:21]>CO>[N+:20]([NH:23][C:24]1[NH:26][C:1](=[O:2])[C:3]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:4][N:25]=1)([O-:22])=[O:21]

参加物

5

反応物 3

HCID 3018359Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionateHCID 10942334Sodium MethoxideHCID 86287517Nitroguanidine

生成物 1

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one収率 27.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of ethyl 2-formyl-3-(6-methyl-3-pyridyl)-propionate (1.55 g) in methanol (20 ml) was added to a stirred solution of sodium methoxide (from 0.161 g sodium) in methanol (20 ml). Dried nitroguanidine (0.73 g) was added and the mixture was heated under reflux overnight and evaporated to dryness. The residue was dissolved in water (50 ml) and the solution was extracted with chloroform and the aqueous phase was adjusted to pH 5 with acetic acid. The solid which precipitated was filtered off and recrystallised from methanol-acetic acid to give 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (0.5 g, 27%), m.p. 215°-6° (decomp).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water (50 ml)
  5. extractionthe solution was extracted with chloroform
  6. customThe solid which precipitated
  7. filtrationwas filtered off
  8. customrecrystallised from methanol-acetic acid

出典と根拠

ORDレコード
ord-bccef702cf3b4d779ecb431689048ca6
出典データセット
uspto-grants-1980_10
特許番号
US04227000

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