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

HRID 1274892Notes

Reaction equation

HRID 1274892 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

A solution of 5.0 g of 5-chloro-6-chloromethyluracil, 6.14 g of 2-iminopyrrolidine and 5.24 g of sodium ethoxide in N,N-dimethylformamide (50 ml) was stirred at room temperature for 14 hours. A crystallized matter was collected by filtration and then suspended in 30 ml of water. After the suspension was neutralized with acetic acid and then washed, an insoluble matter was collected by filtration and then dissolved in 60 ml of 1 N hydrochloric acid. Activated carbon was added to the resultant solution, followed by filtration. The filtrate was concentrated under reduced pressure, and the residue so obtained was washed with ethanol and collected with filtration, whereby 2.68 g of the title compound were obtained (yield: 38%).

Workup

  1. filtrationA crystallized matter was collected by filtration
  2. washwashed
  3. filtrationan insoluble matter was collected by filtration
  4. dissolutiondissolved in 60 ml of 1 N hydrochloric acid
  5. additionActivated carbon was added to the resultant solution
  6. filtrationfollowed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue so obtained
  9. washwas washed with ethanol
  10. filtrationcollected with filtration

Sources & evidence

ORD record
ord-ea883dd9650b4c59b444443c0cbb012b
Source dataset
uspto-grants-2000_12
Patent number
US06159969

Reaction notes

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