Water → 1-{4-[2-(3-Carboxypropionyloxy)ethylaminocarbonyl]butyl}-5-ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1450144Notes

Reaction equation

HRID 1450144 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](OC)=[O:16])[C:4]1=[O:19])[CH3:2].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1.C[N:34]([C:36]1[CH:41]=CC=CN=1)C.[OH2:42]>C(Cl)(Cl)Cl.ClCCl>[C:29]([CH2:28][CH2:27][C:26]([O:31][CH2:41][CH2:36][NH:34][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](=[O:9])[NH:7][C:6]1=[O:10])=[O:16])=[O:32])([OH:30])=[O:42]

Participants

7

Reactant 4

HCID 962WaterHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 1784352455-Ethyl-6-hydroxy-3-(4-methoxycarbonylbutyl)-5-phenyl-2,4(3H,5H)-pyrimidinedione

Product 1

HCID 199751881-{4-[2-(3-Carboxypropionyloxy)ethylaminocarbonyl]butyl}-5-ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the product from step 1 (2.9 g, 0.007 mole), succinic anhydride (0.7 g, 0.007 mole), and dimethylaminopyridine (0.9 g, 0.007 mole) in chloroform (100 mL) was heated with hot water (50°-60° C.) for 30 min and then stirred at room temperature for 3 days. Dichloromethane (300 mL) was added, and the mixture was washed with 10% hydrochloric acid solution (2×100 mL), washed with saturated sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and solvent removed to give an oil which was used directly in the next step.

Workup

  1. washthe mixture was washed with 10% hydrochloric acid solution (2×100 mL)
  2. washwashed with saturated sodium chloride solution (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed
  6. customto give an oil which

Sources & evidence

ORD record
ord-89e4b88de961493f8a97aac142ab3884
Source dataset
uspto-grants-1997_02
Patent number
US05601994

Reaction notes

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