5-Chloro-2(1H)-pyrimidinone → HCID 12795547, compound

HRID 980181Notes

Reaction equation

HRID 980181 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 1202482-Chloro-4'-fluoroacetophenone

Product 1

HCID 12795547HCID 12795547, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one (1.309 g) and 2-chloro-4'-fluoroacetophenone (1.726 g) in triethylamine (2 ml) and ethanol (50 ml) was stirred and heated at reflux for 11/2 hours. After evaporation of solvents, the residue was triturated with water (100 ml). The resulting collected solid was crystallised from ethanol then acetone, but still required purification, by preparative thin-layer chromatography on silica developed in chloroform-ethanol (25:1 v/v), before crystallisation from propan-2-ol to give the title pyrimidinone (204 mg,); 196°-202°; λmaxEtOH 245 nm (ε 17780), 333 nm (ε 2090), λinf 236 nm (ε 15230), 280 nm (ε 980).

Workup

  1. temperatureheated
  2. temperatureat reflux for 11/2 hours
  3. customAfter evaporation of solvents
  4. customthe residue was triturated with water (100 ml)
  5. customThe resulting collected solid
  6. customwas crystallised from ethanol
  7. customacetone, but still required purification
  8. customby preparative thin-layer chromatography on silica developed in chloroform-ethanol (25:1 v/v), before crystallisation from propan-2-ol

Sources & evidence

ORD record
ord-bbc6afbfa8e746e5bc0647d12016a524
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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