Bromomethyl 3-methoxyphenyl ketone → HCID 12795559, compound

HRID 980184Notes

Reaction equation

HRID 980184 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]=[C:15]([O:19][CH3:20])[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][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 12795559HCID 12795559, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one (504 mg) and 2-bromo-3'-methoxyacetophenone (880 mg) in triethylamine (1 ml) and ethanol (50 ml) was stirred at ambient temperature for 20 hours. After evaporation of solvents, the residue was triturated with water (50 ml). The resulting solid was crystallised from ethyl acetate to give the title pyrimidinone (220 mg,); m.p. 134°-137°; λmaxEtOH 249.5 nm (ε 12660), 317 nm (ε 4070), λinf 334.5 nm (ε2950), 344.5 nm (ε 1990).

Workup

  1. customAfter evaporation of solvents
  2. customthe residue was triturated with water (50 ml)
  3. customThe resulting solid was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-5647dcf55a024fa3b167822552d9ed9e
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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