Water → 1-(3,3-Dimethoxy-propyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione

HRID 12692Notes

Reaction equation

HRID 12692 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27].O>CN(C=O)C>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[C:9](=[O:15])[NH:10][C:11]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 589942315-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione

Product 1

HCID 589941601-(3,3-Dimethoxy-propyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep62, 480 mg, 2.32 mmol) and K2CO3 (320 mg, 2.32 mmol) were suspended in dry DMF (6 ml) and stirred at room temperature for 1 h. A solution of 3-bromo-1,1dimethoxy-propane (467 mg, 2.55 mmol) in dry DMF (2 mL) was added dropwise and the mixture stirred at room temperature for 72 hours. Water (80 mL) was added and the product extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 377 mg of the final compound that was used without any other purification in the next step (53% yield).

Workup

  1. stirringthe mixture stirred at room temperature for 72 hours
  2. extractionthe product extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4f6497a025c44772aa97628a9417757c
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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