Diethyl Ether → Ethyl 8-allyl-5-hydroxy-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 224721

반응식

HRID 224721 반응식
C(O[C:4]([C:6]1[C:7]([NH:14][CH2:15][CH:16]=[CH2:17])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.C([CH:20]([C:24](Cl)=[O:25])[C:21](Cl)=[O:22])C.[CH2:27]([O:29]CC)[CH3:28]>>[CH2:27]([O:29][C:24]([C:20]1[C:21](=[O:22])[N:14]([CH2:15][CH:16]=[CH2:17])[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:25])[CH3:28]

참가 물질

4

반응물 3

HCID 3283Diethyl EtherHCID 295704Ethyl 2-methylsulfanyl-4-(prop-2-enylamino)pyrimidine-5-carboxylateHCID 109209242-Ethylpropanedioyl dichloride

생성물 1

HCID 54729613Ethyl 8-allyl-5-hydroxy-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

실험 절차

To a solution of 25.3 g. (0.1 mole) of 4-allylamino-2-methylthio-5-pyrimidine carboxylic acid ethyl ester in 400 ml. of anhydrous diethyl ether was added 7.5 g. (0.005 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in 15 ml. of ethanol and this solution was added to a solution of 2.3 g. (0.1 g. atom) of sodium in 200 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes and was diluted with water, acidified with glacial acetic acid and was extracted with 150 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was acidified with gaseous hydrogen chloride. The mixture was filtered and the filtrate was cooled in ice. The precipitate which formed was collected and was recrystallized from ethyl acetate to give 0.2 g. of product--m.p. 134°-136° C.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in a rotary evaporator
  3. dissolutionThe residue was dissolved in 15 ml
  4. additionof ethanol and this solution was added to a solution of 2.3 g
  5. stirringThe mixture was stirred at room temperature for 5 minutes
  6. additionwas diluted with water
  7. extractionwas extracted with 150 ml
  8. dry with materialThe ether layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. filtrationThe mixture was filtered
  11. temperaturethe filtrate was cooled in ice
  12. customThe precipitate which formed
  13. customwas collected
  14. customwas recrystallized from ethyl acetate
  15. customto give 0.2 g

출처 및 근거

ORD 기록
ord-226c5bb0675d4c8c9100f583d57bd51c
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04233446

연결된 노트

불러오는 중…