Dimethyl Sulfoxide → 1-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1181672

Reaction equation

HRID 1181672 reaction equation
C(OC(=O)C)(=O)C.[C:8]([OH:14])(=O)[CH2:9][C:10]([OH:12])=O.[CH3:15][NH:16][C:17]([NH2:19])=[O:18].CS(C)=O>C(O)(=O)C>[CH3:15][N:16]1[C:8](=[O:14])[CH2:9][C:10](=[O:12])[NH:19][C:17]1=[O:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 11719Methylurea

Product 1

HCID 757221-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

Acetic anhydride (34 ml) was added to a solution of malonic acid (20 g) and methylurea (12.5 g) in acetic acid (46 ml). The mixture was heated to 95° C. for 3 hours then cooled to room temperature. The resulting solution was concentrated under reduced pressure and the residue as 20 mM stock solutions in dimethyl sulphoxide (DMSO, Sigma #D-5879) and serial dilutions were prepared from these solutions using DMSO, 2 μL of which were added to the wells. Activity at room temperature was measured by monitoring the increase in fluorescence using a TECAN Ultra platereader with 340 nm excitation and 465 nm emission filters. The compounds provided have measured IC50 of less then 400 μM

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue as 20 mM stock solutions in dimethyl sulphoxide (DMSO, Sigma #D-5879) and serial dilutions were prepared from these solutions
  4. additionwere added to the wells
  5. customat room temperature
  6. temperatureincrease in fluorescence
  7. customThe compounds provided

Sources & evidence

ORD record
ord-13c17c6528dd44a7adb4f6d33a066515
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Linked notes

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