5-Chloro-2(1H)-pyrimidinone → 5-Chloro-1-(4-methylsulphinylphenacyl)pyrimidin-2-one

HRID 980180Notes

Reaction equation

HRID 980180 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][C:16]([S:19]([CH3:21])=[O:20])=[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]([S:19]([CH3:21])=[O:20])=[CH:15][CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 127955374-Methylsulphinylphenacyl bromide

Product 1

HCID 127955465-Chloro-1-(4-methylsulphinylphenacyl)pyrimidin-2-oneYield 54.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (399 mg). and 2-bromo-4'-methylsulphinylacetophenone (784 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour, when the resulting suspension was chilled in ice. The collected solid was crystallised from ethanol to give the title pyrimidinone (509 mg,); m.p. 219°-220°; λmaxEtOH 233.5 nm (ε 17920), 332 nm (ε 2060), λinf 266 nm (ε 9280).

Workup

  1. temperaturewhen the resulting suspension was chilled in ice
  2. customThe collected solid was crystallised from ethanol

Sources & evidence

ORD record
ord-f6f43282221c4ea9a03bb8905fb42953
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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