Sodium ethoxide → 2-[2-(2-Thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

HRID 1719147노트

반응식

HRID 1719147 반응식
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[O-]CC.[Na+].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O>C(O)C>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideHCID 135053102-(2-Thienylmethylthio)ethylamine hydrochloride

생성물 1

HCID 135052962-[2-(2-Thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

2-(2-Thienylmethylthio)ethylamine hydrochloride (2 g) in ethanol (25 ml) was added to a solution of sodium ethoxide (prepared from 0.218 g sodium) in ethanol and the mixture was stirred for 0.5 hour. 2-Nitroamino-5-(3-pyridylmethyl)-4-pyrimidone (2.34 g) was added and the mixture was boiled under reflux for 40 hours and evaporated to dryness. Pyridine (50 ml) was added to the residue and the mixture was boiled under reflux for 24 hours and evaporated. The residue was crystallised from ethanol/ethyl acetate and further purified by elution from a column of silica gel with ethyl acetate/methanol (5.1) and recrystallisation from 2-propanol to give 2-[2-(2-thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone m.p. 145°-148°.

후처리

  1. temperatureunder reflux for 40 hours
  2. customevaporated to dryness
  3. additionPyridine (50 ml) was added to the residue
  4. temperatureunder reflux for 24 hours
  5. customevaporated
  6. customThe residue was crystallised from ethanol/ethyl acetate
  7. customfurther purified by elution from a column of silica gel with ethyl acetate/methanol (5.1) and recrystallisation from 2-propanol

출처 및 근거

ORD 기록
ord-fd4d128f087b48c6a162290efccaca34
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539207

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