Phenacyl bromide → 5-Iodo-1-phenacylpyrimidin-2-one

HRID 980168Notes

Reaction equation

HRID 980168 reaction equation
[I: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][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[I: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][CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 119590965-Iodopyrimidin-2-ol

Product 1

HCID 127955355-Iodo-1-phenacylpyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-iodopyrimidin-2-one (556 mg) and α-bromoacetophenone (533 mg) in triethylamine (0.5 ml) and ethanol (50 ml) was stirred at ambient temperature for 71/2 hours. The resulting solution was evaporated and the residue triturated with water. This product was purified by preparative thin-layer chromatography on silica before crystallisation from ethyl acetate to give the title pyrimidinone: yield 253 mg: m.p. 155°-157°: λmaxEtOH 238.5 nm (ε 23070), 340 nm (ε 2400), λinf 250 nm (ε 17160), 275 nm (ε 1780).

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue triturated with water
  3. customThis product was purified by preparative thin-layer chromatography on silica before crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e03a08e39a184094a14204bdf2a65dc9
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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