Hydrochloric Acid → HCID 59363805, compound

HRID 2189163Notes

Reaction equation

HRID 2189163 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][O:24][CH3:25])=O)=[CH:7][C:6]=1[CH2:27][CH3:28])(=O)C.[NH2:29][C:30]([NH2:32])=[O:31].Cl>O1CCOCC1>[CH2:27]([C:6]1[CH:7]=[C:8]([C:11]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:22][CH2:23][O:24][CH3:25])[NH:32][C:30](=[O:31])[N:29]=2)[CH:9]=[CH:10][C:5]=1[NH2:4])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 68603776HCID 68603776, compound

Product 1

HCID 59363805HCID 59363805, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A flask was charged with 1-(4-acetamido-3-ethylphenyl)-3-(2-(2-methoxyethoxy)phenyl)propane-1,3-dione (4.0 g, 10.4 mmol), urea (3.0 g, 50 mmol) and 4 N HCl in dioxane (80 mL). The mixture was heated to 110° C. overnight. The reaction was cooled down, concentrated, neutralized with sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to result in 4-(2-ethylanilin-4-yl)-6-[2-(2-methoxyethoxy)phenyl]pyrimidin-2(1H)-one as a white solid.

Workup

  1. temperatureThe reaction was cooled down
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. customto result in 4-(2-ethylanilin-4-yl)-6-[2-(2-methoxyethoxy)phenyl]pyrimidin-2(1H)-one as a white solid

Sources & evidence

ORD record
ord-d2a11b1f399349dfa697b7634d17d889
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

Loading…