Sodium ethoxide → 5-Chloro-6-(1-(2-iminopyrrolidinyl) methyl)uracil hydrochloride

HRID 1017501Notes

Reaction equation

HRID 1017501 reaction equation
[Cl:1][C:2]1[C:3](=[O:11])[NH:4][C:5](=[O:10])[NH:6][C:7]=1[CH2:8]Cl.[NH:12]=[C:13]1[CH2:17][CH2:16][CH2:15][NH:14]1.[O-]CC.[Na+]>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[C:3](=[O:11])[NH:4][C:5](=[O:10])[NH:6][C:7]=1[CH2:8][N:14]1[CH2:15][CH2:16][CH2:17][C:13]1=[NH:12]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 41710565-Chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 178507686HCID 178507686, compound

Product 1

HCID 99037785-Chloro-6-(1-(2-iminopyrrolidinyl) methyl)uracil hydrochlorideYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-6-chloromethyluracil (5.0 g), 2-iminopyrrolidine (6.14 g), and sodium ethoxide (5.24 g) were dissolved in N,N-dimethylformamide (50 ml) and the resultant solution was stirred for 14 hours at room temperature. Subsequently, precipitated crystals were collected through filtration, and the crystals were suspended in water (30 ml). The resultant suspension was neutralized with acetic acid and washed. Subsequently, insoluble matter was collected through filtration and was dissolved in 1N HCl (60 ml). Activated carbon was added to the resultant solution and the mixture was subjected to filtration. The filtrate was concentrated under reduced pressure, and the residue was washed with ethanol, followed by filtration, to thereby obtain 2.68 g of the title compound (38% yield).

Workup

  1. customSubsequently, precipitated crystals
  2. filtrationwere collected through filtration
  3. washwashed
  4. filtrationSubsequently, insoluble matter was collected through filtration
  5. dissolutionwas dissolved in 1N HCl (60 ml)
  6. additionActivated carbon was added to the resultant solution
  7. filtrationthe mixture was subjected to filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. washthe residue was washed with ethanol
  10. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-244ee05fe5d64339b42ff3a29d704f61
Source dataset
uspto-grants-2002_11
Patent number
US06479500B1

Reaction notes

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