HCID 3991306, compound → 3-benzyl-5-methyl-1H-pyrimidine-2,4-dione

HRID 342539Notes

Reaction equation

HRID 342539 reaction equation
C([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23])C1C=CC=CC=1>[Pd].C([O-])=O.[NH4+]>[CH2:16]([N:10]1[C:11](=[O:15])[C:12]([CH3:14])=[CH:13][NH:8][C:9]1=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 3991306HCID 3991306, compound

Product 1

HCID 111719463-benzyl-5-methyl-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2723923Ammonium formateSolvent

Procedure

A mixture of 1,3-dibenzyl-5-methyl-2,4(1H,3H)-pyrimidinedione (2 g, 6.5 mmol), 5% palladium on carbon (3 g) and 0.4N ammonium formate (250 mL in methanol) was heated 1.5 hours at reflux. The reaction mixture then was filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (95:5) to give 3-benzyl-5-methyl-2,4(1H,3H)-pyrimidinedione, m.p. 208°-210° C.

Workup

  1. temperaturewas heated 1.5 hours
  2. temperatureat reflux
  3. filtrationThe reaction mixture then was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-967537bb05594edb93591d4f289536eb
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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