5-Chloro-2(1H)-pyrimidinone → HCID 20491782, compound

HRID 434659Notes

Reaction equation

HRID 434659 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])O.[Na+].[CH2:14]=[C:15]1[CH2:20][O:19][C:17](=[O:18])[CH2:16]1>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:14][CH:15]2[CH2:20][O:19][C:17](=[O:18])[CH2:16]2)[CH:7]=1

Participants

5

Reactant 3

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 516892Sodium BicarbonateHCID 123033602(3H)-Furanone, dihydro-4-methylene-

Product 1

HCID 20491782HCID 20491782, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (1.007 g) and sodium hydrogen carbonate (647 mg) in 3-methylene-γ-butyrolactone (1.208 g) and ethanol (50 ml) was stirred and heated at reflux. After 2 h, the suspension was cooled and filtered. The filtrate was evaporated and the residue and solid were combined and boiled in ethyl acetate (150 ml). The resulting suspension was filtered and the filtrate evaporated to a pale cream solid. The solid from the filtration was treated with water (50 ml) and the resulting suspension filtered to give a solid which was combined with the pale cream solid and recrystallised from methanol to give white crystals of the title pyrimidinone (424 mg), m.p. 283°-284° C., λmax (EtOH) 229.5 nm (ε 7,700), 332 nm (ε 2,100).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperaturethe suspension was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. filtrationThe resulting suspension was filtered
  7. customthe filtrate evaporated to a pale cream solid
  8. filtrationThe solid from the filtration
  9. additionwas treated with water (50 ml)
  10. filtrationthe resulting suspension filtered
  11. customto give a solid which
  12. customrecrystallised from methanol

Sources & evidence

ORD record
ord-e97544ef8469477ca75b12a99d36b46d
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

Loading…