Ethanone, 2-chloro-1,2-diphenyl- → 5-Chloro-1-desylpyrimidin-2-one

HRID 980188

Reaction equation

HRID 980188 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:9]1([C:15]([CH:17](Cl)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 127955605-Chloro-1-desylpyrimidin-2-oneYield 40.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one (406 mg) and desyl chloride (2-chloro-2-phenyl acetophenone) (692 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour, then heated at reflux for 11/2 hours. After evaporation of solvents, the residue was dissolved in ethyl acetate (150 ml). The solution was washed with water (100 ml), dried (MgSO4) and evaporated to a foam which was crystallised from ethyl acetate to give the title pyrimidinone (393 mg,); m.p. 145°-146°; λmaxEtOH 230 nm (ε 15960), 250 nm (ε 15000), 335 nm (ε 4700), λinf 262.5 nm (ε 8400), 269 n, (ε 4420).

Workup

  1. temperatureheated
  2. temperatureat reflux for 11/2 hours
  3. customAfter evaporation of solvents
  4. dissolutionthe residue was dissolved in ethyl acetate (150 ml)
  5. washThe solution was washed with water (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated to a foam which
  8. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-2905d1c3fd6d472aaa0b555daf5e4aae
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Linked notes

Loading…