Potassium Carbonate → HCID 18918924, compound

HRID 1291388Notes

Reaction equation

HRID 1291388 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14]3[N:15]=[C:16]4[CH:25]=[CH:24][CH:23]=[CH:22][N:17]4[C:18](=[O:21])[C:19]=3[CH3:20])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][Cl:38])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:38].[CH3:20][C:19]1[C:18](=[O:21])[N:17]2[CH:22]=[CH:23][CH:24]=[CH:25][C:16]2=[N:15][C:14]=1[O:13][CH2:12][C:11]1[CH:26]=[CH:27][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:37][C:34]3[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=3)=[CH:29][CH:28]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 189188752-[4-(4-hydroxybenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 18918924HCID 18918924, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (96 mg), 4-picolyl chloride hydrochloride (89 mg) and potassium carbonate (178 mg) in DMF (7 ml) was stirred at room temperature for 13 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane: methanol =20:1) and treated with hydrogen chloride/ethyl acetate to provide the title compound as colorless solid (87 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (dichloromethane: methanol =20:1)
  7. additiontreated with hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-8e2b41665e174c589f379865b90ad776
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…