5-Chloro-2(1H)-pyrimidinone → HCID 12795558, compound

HRID 980183Notes

Reaction equation

HRID 980183 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[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][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 123440Bromomethyl 2-methoxyphenyl ketone

Product 1

HCID 12795558HCID 12795558, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one (541 mg) and 2-bromo-2'-methoxyacetophenone (954 mg) in triethylamine (1 ml) and ethanol (25 ml) was stirred at ambient temperature for 31/2 hours. After evaporation of solvents, the residue was dissolved in ethyl acetate (150 ml) and this solution was washed with water (50 ml) and brine (25 ml), dried (MgSO4) and evaporated to give a foam. This was purified by preparative thin-layer chromatography on silica, developed in chloroform, then chloroform-ethanol (25:1) before crystallisation from ethyl acetate to give the title pyrimidinone (347 mg,); m.p. 123°-125°; λmax 248.5 nm ε 12200), 317.5 nm (ε 6700), λinf 229.5 nm (ε 12440), 349 nm (ε 2640).

Workup

  1. customAfter evaporation of solvents
  2. dissolutionthe residue was dissolved in ethyl acetate (150 ml)
  3. washthis solution was washed with water (50 ml) and brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a foam
  7. customThis was purified by preparative thin-layer chromatography on silica
  8. customchloroform-ethanol (25:1) before crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-f09500eee4de44d5bc1638e3bc9e6bbb
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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