Iodine → 6-ethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone

HRID 1448

Reaction equation

HRID 1448 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:15])[CH:4]=1)[CH3:2].[OH-].[Na+].[I:18]I>O>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:15])[C:4]=1[I:18])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 1356298226-Ethyl-2-phenylpyrimidin-4(1H)-one

Product 1

HCID 1358375326-ethyl-5-iodo-2-phenyl-4(3H)-pyrimidinoneYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8.18 g (40.9 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone, 1.68 g (42.0 mmol) of sodium hydroxide, 10.42 g (41.0 mmol) of iodine and 50 mL of water was heated at 50° C. for 4 h. The mixture was cooled and filtered. The white solid collected was dried in a vacuum oven to leave 12.60 g (75%) of 6-ethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone. 1 H-NMR (d6-DMSO) δ 1.25(3H,t), 2.85(2H,q), 7.50(3H,m), 8.15(2H,m).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customThe white solid collected
  4. customwas dried in a vacuum oven

Sources & evidence

ORD record
ord-be4d8163d3b146d0a463a6fc363aaeaa
Source dataset
uspto-grants-1998_03
Patent number
US05726124

Linked notes

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