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

HRID 224873

반응식

HRID 224873 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate (1.55 g) in methanol (20 ml) was added to a solution of sodium methoxide (from 0.161 g sodium) in methanol (20 ml). Dried nitroguanidine (0.729 g) was added over 5 minutes and the mixture was stirred and boiled under reflux overnight and evaporated to dryness. The residue was dissolved in water (50 ml) and the solution was extracted with chloroform (2×25 ml, discarded) and acidified to pH 5 with acetic acid. The solid which precipitated out was filtered off and recrystallised from methanol-acetic acid to give 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (0.5 g) m.p. 215°-216° (decomp.).

후처리

  1. temperatureunder reflux overnight
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionthe solution was extracted with chloroform (2×25 ml, discarded)
  5. customThe solid which precipitated out
  6. filtrationwas filtered off
  7. customrecrystallised from methanol-acetic acid

출처 및 근거

ORD 기록
ord-46642644a8ee4d13ad3d1e29c7f3f7da
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04234588

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