6-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione → HCID 23324666, compound

HRID 1380839Notes

Reaction equation

HRID 1380839 reaction equation
Cl[CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.[C:11]([O-:14])(=[O:13])[CH3:12].[Na+]>C(O)(=O)C.[I-].[Na+]>[C:11]([O:14][CH2:2][C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 517045Sodium Acetate

Product 1

HCID 23324666HCID 23324666, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 16.05 g (0.10 mol) of 6-chloromethyl-uracil, 9.85 g (0.12 mol) of sodium acetate and 0.3 g of sodium iodide in 50 ml of glacial acetic acid is heated at reflux for 20 minutes. The mixture is subsequently cooled to room temperature and filtered. The filtrate is treated with 250 ml of diethyl ether and the resulting crystals are filtered off. The combined crystallizate is added to 200 ml of water and thus liberated from the residual salts. 11.3 g of 6-acetoxymethyl-uracil are isolated by filtration.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 minutes
  3. filtrationfiltered
  4. additionThe filtrate is treated with 250 ml of diethyl ether
  5. filtrationthe resulting crystals are filtered off
  6. additionThe combined crystallizate is added to 200 ml of water

Sources & evidence

ORD record
ord-b43bf919fa8b47999a12d590b09046e8
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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