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

HRID 980172Notes

Reaction equation

HRID 980172 reaction equation
[F: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>[F: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 1014985-Fluoropyrimidin-2-one

Product 1

HCID 127955365-Fluoro-1-phenacylpyrimidin-2-oneYield 21.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-fluoropyrimidin-2-one (480 mg) and α-bromoacetophenone (843 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 31/2 hours. The resulting suspension was chilled in ice. The solid was collected by filtration, then crystallised twice from ethanol to give the title pyrimidinone (206 mg yield); m.p. 167°-175°, λmaxEtOH 243 nm (ε 15110), 331 nm (ε 3590), λinf 283 nm (ε 1870), 290 nm (ε 1890), 344 nm (ε 2740).

Workup

  1. temperatureThe resulting suspension was chilled in ice
  2. filtrationThe solid was collected by filtration
  3. customcrystallised twice from ethanol

Sources & evidence

ORD record
ord-a981d926bc0c4f74a779d2e63514cdf6
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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