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

HRID 127381

반응식

HRID 127381 반응식
C(O[C:4]([C:6]1[C:7]([NH:14][CH3:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.C([CH:18]([C:22](Cl)=[O:23])[C:19](Cl)=[O:20])C.[CH2:25]([O:27]CC)[CH3:26]>>[CH2:25]([O:27][C:22]([C:18]1[C:19](=[O:20])[N:14]([CH3:15])[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:23])[CH3:26]

참가 물질

4

반응물 3

HCID 3283Diethyl EtherHCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 109209242-Ethylpropanedioyl dichloride

생성물 1

HCID 54729611Ethyl 5-hydroxy-8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

실험 절차

To a solution of 4.54 g. (0.02 mole) of 4-methylamino-2-methylthio-5-pyrimidine carboxylic acid ethyl ester in 100 ml. of anhydrous diethyl ether was added 1.5 g. (0.01 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with a few ml. of diethyl ether and was filtered. The filtrate was evaporated and the residue was dissolved in 10 ml. of ethanol. This solution was added to a solution of 0.37 g. (0.015 g atom) of sodium in 20 ml. of ethanol. The mixture was stirred at room temperature for 10 minutes. The mixture was diluted with water and was acidified with glacial acetic acid. The precipitate which formed was collected, air dried and was recrystallized from ethanol to afford 0.4 g. of title product--m.p. 166°-168° C.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in a rotary evaporator
  3. customThe residue was triturated with a few ml
  4. filtrationof diethyl ether and was filtered
  5. customThe filtrate was evaporated
  6. dissolutionthe residue was dissolved in 10 ml
  7. additionThis solution was added to a solution of 0.37 g
  8. stirringThe mixture was stirred at room temperature for 10 minutes
  9. additionThe mixture was diluted with water
  10. customThe precipitate which formed
  11. customwas collected
  12. customair dried
  13. customwas recrystallized from ethanol
  14. customto afford 0.4 g

출처 및 근거

ORD 기록
ord-0548e7b846884300a395705221d95de2
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04255568

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