Malonic Acid → 1,3-Dipropylpyrimidine-2,4,6(1H,3H,5H)-trione

HRID 437536Notes

Reaction equation

HRID 437536 reaction equation
[CH2:1]([NH:4][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:2][CH3:3].[C:11]([OH:17])(=O)[CH2:12][C:13]([OH:15])=O.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH2:1]([N:4]1[C:11](=[O:17])[CH2:12][C:13](=[O:15])[N:7]([CH2:8][CH2:9][CH3:10])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 69343N,N'-Dipropylurea

Product 1

HCID 124709161,3-Dipropylpyrimidine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Synthesis was carried out according to the procedure of Goldner, Ann. Chem., 691, 142 (1966) using 1,3-di-n-propylurea (777 g., 5.38 mole), malonic acid (660 g., 6.34 mole), glacial acetic acid (1050 ml.) and acetic anhydride (2160 ml.) to obtain 790 g. (69.2%) of product, melting point 77° - 80° C. NMR and IR spectra were consistent with the assigned structure.

Workup

  1. customSynthesis
  2. customto obtain 790 g

Sources & evidence

ORD record
ord-713a4702711a4589846a6d9a408246de
Source dataset
uspto-grants-1977_06
Patent number
US04031218

Reaction notes

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