Iodoethane → HCID 59833620, compound

HRID 269796Notes

Reaction equation

HRID 269796 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[N+:13]([O-:15])=[O:14].C([O-])([O-])=O.[K+].[K+].I[CH2:23][CH3:24]>CN(C=O)C>[CH3:1][C:2]1[N:7]([CH2:23][CH3:24])[C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 102626226-methyl-5-nitro-3-propyl-1,3-dihydropyrimidine-2,4-dione

Product 1

HCID 59833620HCID 59833620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of the nitro derivative, 6-methyl-5-nitro-3-propyl-1,3-dihydropyrimidine-2,4-dione prepared in Example 5 (1.56 g) and K2CO3 (3.0 g) in DMF was added iodoethane. The reaction mixture was heated at 80° C. for 3 h. After completion of the starting material, K2CO3 was filtered and DMF was distilled off. The residue was dissolved in ethyl acetate, washed with water, brine and dried over Na2SO4 Removal of solvent furnished the product as yellow oil, which was purified using flash chromatography. Elution with 30% ethyl acetate/hexane furnished the material as white solid, which was characterized by using NMR and mass.

Workup

  1. filtrationAfter completion of the starting material, K2CO3 was filtered
  2. distillationDMF was distilled off
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4 Removal of solvent

Sources & evidence

ORD record
ord-d41b9585de3445d3bb920373090821ba
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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