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

HRID 440979Notes

Reaction equation

HRID 440979 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-423d9b459df045f19e3c6f5b17ff986a
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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