Potassium Carbonate → 2-[4-(4-hydroxybenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1291393Notes

Reaction equation

HRID 1291393 reaction equation
[OH:1][C:2]1[N:3]=[C:4]2[CH:13]=[CH:12][CH:11]=[CH:10][N:5]2[C:6](=[O:9])[C:7]=1[CH3:8].[Si]([O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:8][C:7]1[C:6](=[O:9])[N:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]2=[N:3][C:2]=1[O:1][CH2:32][C:31]1[CH:30]=[CH:29][C:28]([C:26](=[O:27])[C:25]2[CH:36]=[CH:37][C:22]([OH:21])=[CH:23][CH:24]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18918912HCID 18918912, compoundHCID 135448456HCID 135448456, compound

Product 1

HCID 189188752-[4-(4-hydroxybenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneYield 4.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxy-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (3.158 g), 4-(4-t-butyldimethylsilyloxybenzoyl)benzyl bromide (12.24 g) and potassium carbonate (5.07 g) in DMF (50 ml) was stirred at room temperature for 24 hours. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate =1:2) and recrystallized from chloroform-methanol-ethyl acetate to provide the title compound as colorless solid (325 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate =1:2)
  3. customrecrystallized from chloroform-methanol-ethyl acetate

Sources & evidence

ORD record
ord-2e836f995f4b49089e9108168dc40fae
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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