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

HRID 1358227Notes

Reaction equation

HRID 1358227 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-imino pyrrolidine and 5.24 g of sodium ethoxide in 50 ml of N,N-dimethylformamide was stirred at room temperature for 14 hours. The resulting crystals were collected by filtration and suspended in 30 ml of water. The suspension was neutralized with acetic acid and washed. The insoluble substances were collected by filtration and dissolved in 60 ml of 1N hydrochloric acid. After addition of activated carbon, the resulting mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was washed with ethanol and collected by filtration, giving 2.68 g of the desired compound (yield 38%). The physical properties of this compound are as follows:

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed
  3. filtrationThe insoluble substances were collected by filtration
  4. dissolutiondissolved in 60 ml of 1N hydrochloric acid
  5. additionAfter addition of activated carbon
  6. filtrationthe resulting mixture was filtered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe residue was washed with ethanol
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0be4a01814f343d78cd2737a0230425c
Source dataset
uspto-grants-2003_07
Patent number
US06596720B1

Reaction notes

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