2-Bromobenzyl bromide → 9-[(o-Bromobenzyl)oxy]-4-oxo-4H-pyrido[1,2-alpha] pyrimidine-3-carboxylic Acid, Ethyl Ester

HRID 1657364Notes

Reaction equation

HRID 1657364 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]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br.C(=O)(O)[O-].[K+]>CC(CC)=O>[Br:18][C:19]1[CH:26]=[CH:25][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 769652-Bromobenzyl bromideHCID 516893Potassium BicarbonateHCID 616445Ethyl 9-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate

Product 1

HCID 122199929-[(o-Bromobenzyl)oxy]-4-oxo-4H-pyrido[1,2-alpha] pyrimidine-3-carboxylic Acid, Ethyl EsterYield 85.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 4.7 g of 9-hydroxy-4-oxo-4H-pyrido-[1,2-α] pyrimidine-3-carboxylic acid, ethyl ester, 7.2 g of o-bromobenzyl bromide, and 200 ml of ethyl methyl ketone is added 4.0 g of anhydrous potassium bicarbonate, and the mixture is stirred and heated under reflux for 18 hours. The cooled mixture is filtered and the filtrate is concentrated in vacuo to give a solid residue. This is recrystallized successively from 1:1 toluene-skellysolve and from 2-propanol to give about 6.9 g of the named product, m.p. about 164°-166°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe cooled mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto give a solid residue
  6. customThis is recrystallized successively from 1:1 toluene-skellysolve and from 2-propanol

Sources & evidence

ORD record
ord-416b369796bf46728bf3867162605968
Source dataset
uspto-grants-1976_06
Patent number
US03960847

Reaction notes

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