N,N'-Dimethylurea → 6-(3-pyridyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

HRID 1253055Notes

Reaction equation

HRID 1253055 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:15][NH:16][C:17]([NH:19][CH3:20])=[O:18].C(=O)(O)[O-].[Na+]>Cl.C(O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]2[N:19]([CH3:20])[C:17](=[O:18])[N:16]([CH3:15])[C:10](=[O:12])[CH:9]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 7293N,N'-DimethylureaHCID 222197Ethyl 3-oxo-3-(pyridin-3-yl)propanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 140964686-(3-pyridyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneYield 35.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a mixture of ethyl nicotinoylacetate (2.30 g) and N,N'-dimethylurea (1.05 g) were added conc. hydrochloric acid (a few drops) and ethanol (1 ml) and the mixture was stirred at 110°-115° C. for 4 hours under reduced pressure (30 mmHg). After being cooled to ambient temperature, the solution was adjusted to pH 7.0 with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated to give 6-(3-pyridyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (0.91 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-87dda7ca042841a5abcc77be35a8419f
Source dataset
uspto-grants-1988_05
Patent number
US04746664

Reaction notes

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