Triethylamine → 5-Benzyluracil

HRID 1975488Notes

Reaction equation

HRID 1975488 reaction equation
[CH2:1]([C:8]1[C:9](=[O:20])[NH:10][C:11](=[O:19])[NH:12][C:13]=1OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[OH-].[Na+]>CO.[Pd]>[CH2:1]([C:8]1[C:9](=[O:20])[NH:10][C:11](=[O:19])[NH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 11141002HCID 11141002, compound

Product 1

HCID 2362125-BenzyluracilYield 79.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-benzyl-6-methanesulphonyloxy-2,4-(1H,3H)-pyrimidinedione (3 g) and Et3N (2.1 ml) in MeOH was hydrogenated in the presence of Pd/C 5% (0.3 g) for 3 hr at 35° C. NaOH 5% (2.5 eq) was added and the catalyst filtered off. The solution was acidified to pH 2 with HCl 10%. The precipitated white solid was then collected by filtration, washed with water, ether and dried under vacuum to yield the desired 5-benzyl-2,4-(1H,3H)-pyrimidinedione: 1.635 g, 79.8% yield.

Workup

  1. filtrationthe catalyst filtered off
  2. filtrationThe precipitated white solid was then collected by filtration
  3. washwashed with water, ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a1c6c60505fc4ebcb2e1361cee514383
Source dataset
uspto-grants-1994_02
Patent number
US05286861

Reaction notes

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