Carbonic acid-guanidine (1:1) → 2-amino-6-ethyl-5-(3-undecylphenoxy)-1H-pyrimidin-4-one

HRID 440979노트

반응식

HRID 440979 반응식
[CH2:1]([C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=1)[O:15][CH:16]([C:22](=O)[CH2:23][CH3:24])[C:17](OCC)=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(=O)(O)O.[NH2:33][C:34]([NH2:36])=[NH:35]>C(O)C>[NH2:36][C:34]1[N:35]=[C:17]([OH:18])[C:16]([O:15][C:14]2[CH:26]=[CH:27][CH:28]=[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:13]=2)=[C:22]([CH2:23][CH3:24])[N:33]=1

참가 물질

4

반응물 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 19955508Ethyl 2-(3-undecylphenoxy)-3-oxopentanoate

생성물 1

HCID 1784428062-amino-6-ethyl-5-(3-undecylphenoxy)-1H-pyrimidin-4-one수율 15.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A stirred solution of 8.9 grams (0.028 mole) of ethyl 2-(3-undecylphenoxy)-3-oxopentanoate and 2.5 grams (0.028 mole) of guanidine carbonate in 30 mL of ethanol was heated at reflux for about 6 hours. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was taken up in 50 mL of water and 5 mL of acetic acid, and the mixture was extracted with 50 mL of diethyl ether. The ether layer was extracted with 20 grams of aqueous 10% sodium hydroxide and then with 100 mL of water. The water extract was made acidic with acetic acid, and then it was extracted with 50 mL of diethyl ether. The ether extract was concentrated under reduced pressure to a residue. The residue was then taken up in 25 mL of heptane, and the mixture was again concentrated under reduced pressure to a residual solid. The solid was slurried in an additional 25 mL of heptane, and then it was collected by filtration. The solid was dried under reduced pressure, yielding 1.7 grams of 2-amino-6-ethyl-4-hydroxy-5-(3-undecylphenoxy) pyrimidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperatureat reflux for about 6 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure to a residue
  3. extraction5 mL of acetic acid, and the mixture was extracted with 50 mL of diethyl ether
  4. extractionThe ether layer was extracted with 20 grams of aqueous 10% sodium hydroxide
  5. extractionThe water extract
  6. extractionit was extracted with 50 mL of diethyl ether
  7. extractionThe ether extract
  8. concentrationwas concentrated under reduced pressure to a residue
  9. concentrationthe mixture was again concentrated under reduced pressure to a residual solid
  10. filtrationit was collected by filtration
  11. customThe solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-423d9b459df045f19e3c6f5b17ff986a
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521192

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