Water → HCID 178435246, compound

HRID 1450142Notes

Reaction equation

HRID 1450142 reaction equation
[CH2:1]([C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([OH:9])=[N:7][C:6](=[O:10])[N:5]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[C:4]1=[O:19])[CH3:2].O>O1CCOCC1.Cl>[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:5]1[C:4](=[O:19])[C:3]([CH2:1][CH3:2])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]([OH:9])=[N:7][C:6]1=[O:10])([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 962WaterHCID 1784352455-Ethyl-6-hydroxy-3-(4-methoxycarbonylbutyl)-5-phenyl-2,4(3H,5H)-pyrimidinedione

Product 1

HCID 178435246HCID 178435246, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The 5-ethyl-6-hydroxy-3-(4-methoxy-carbonylbutyl)-5-phenyl-2,4 (3H,5H)-pyrimidinedione ester (54.0 g, 0.156 mole) of step 1 in dioxane (500 mL), concentrated hydrochloric acid (55 mL), and water (55 mL) was heated at reflux for 4 hrs and at room temperature overnight. The dioxane was removed under reduced pressure, and saturated sodium chloride solution (250 mL) and dichloromethane (400 mL) were added to the residue. The organic layer was separated, and the aqueous solution was extracted with dichloromethane (3×150 mL). The combined organic solutions were washed with saturated sodium chloride solution (200 mL), dried over anhydrous MgSO4, filtered, and the solvent removed. To the residue was added diethyl ether, and the mixture was placed in a freezer at -16° C. over the weekend, and then filtered.

Workup

  1. customThe dioxane was removed under reduced pressure, and saturated sodium chloride solution (250 mL) and dichloromethane (400 mL)
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. extractionthe aqueous solution was extracted with dichloromethane (3×150 mL)
  5. washThe combined organic solutions were washed with saturated sodium chloride solution (200 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. additionTo the residue was added diethyl ether
  10. customwas placed in a freezer at -16° C. over the weekend
  11. filtrationfiltered

Sources & evidence

ORD record
ord-21c1f31699e848e3ad5d8b99fb2c1c50
Source dataset
uspto-grants-1997_02
Patent number
US05601994

Reaction notes

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