Benzylurea → 3-benzyl-5-isopropylpyrimidine-2,4,6(1H,3H)-trione

HRID 357121

Reaction equation

HRID 357121 reaction equation
[CH2:1]([NH:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]([CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]([CH:12]([CH3:14])[CH3:13])[C:21](=[O:22])[NH:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10853BenzylureaHCID 12966Diethyl isopropylmalonateHCID 10942334Sodium Methoxide

Product 1

HCID 189367373-benzyl-5-isopropylpyrimidine-2,4,6(1H,3H)-trione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 22.53 g (150 mmol) of benzylurea and 30.34 g (150 mmol) of diethyl isopropylmalonate in 77 ml of methanol, 36.6 ml (150 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 34.96 g (89.5%, white crystal) of the desired product.

Workup

  1. additionwas added at room temperature
  2. temperatureby refluxing for 16 hours
  3. temperatureAfter the reaction mixture was cooled
  4. distillationthe solvent was distilled off
  5. dissolutionAfter the residue was dissolved in water
  6. filtrationinsoluble substances were filtered out
  7. additionby adding concentrated hydrochloric acid
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water and n-hexane-diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-f241c9c163a448a881cb080e419c07a2
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Linked notes

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