Potassium Carbonate → 9-[(2-Bromo-4-chlorobenzyl)oxy]-4-oxo-4H-pyrido [1,2-alpha]pyrimidine-3-carboxylic Acid, Ethyl Ester

HRID 1657363Notes

Reaction equation

HRID 1657363 reaction equation
[OH:1][C:2]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[Br:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21][O:1][C:2]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 616445Ethyl 9-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylateHCID 106130662-Bromo-1-(bromomethyl)-4-chlorobenzene

Product 1

HCID 1317102559-[(2-Bromo-4-chlorobenzyl)oxy]-4-oxo-4H-pyrido [1,2-alpha]pyrimidine-3-carboxylic Acid, Ethyl EsterYield 108.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 4.7 g of 9-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carboxylic acid, ethyl ester, 7.2 g of 2-bromo-4-chlorobenzyl bromide and 200 ml of ethyl methyl ketone is added 3.3 g of anhydrous potassium carbonate. The mixture is stirred and heated under reflux for 18 hours, cooled and filtered. The filtrate is concentrated in vacuo to give 9.5 g of a viscous gum. This is dissolved in 100 ml of chloroform and the chloroform solution is washed with 60 ml of 5% aqueous potassium hydroxide. The chloroform solution is separated, washed with 25 ml of saturated aqueous sodium chloride, dried, and concentrated to give 7.4 g of a viscous gum. This gum is crystallized in 250 ml of 1:1 toluene-Skellysolve E to give 3.6 g of green crystals that sinter at 155° and melt at 162°-165°. A second recrystallization from 225 ml of 2-propanol gives the yellow crystalline named product, m.p. about 167°-169°. The yield is about 2.95 g.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-75294a8ca3e6409bb55b46a17c3cfa07
Source dataset
uspto-grants-1976_06
Patent number
US03960847

Reaction notes

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