Potassium Carbonate → 6-Ethyl-7-methyl-1-[4-[4-(2-morpholinoethoxy)benzoyl]benzyl]imidazo[1,2-a]pyrimidin-5(1H)-one hydrochloride

HRID 1291384Notes

Reaction equation

HRID 1291384 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:6]2=[N:5][C:4]=1[CH3:29])[CH3:2].Cl.[Cl:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:31].[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:28])[C:21]4[CH:22]=[CH:23][C:24]([O:27][CH2:32][CH2:33][N:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[CH:25][CH:26]=4)=[CH:16][CH:15]=3)[C:6]2=[N:5][C:4]=1[CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 189189466-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-one

Product 1

HCID 189191216-Ethyl-7-methyl-1-[4-[4-(2-morpholinoethoxy)benzoyl]benzyl]imidazo[1,2-a]pyrimidin-5(1H)-one hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-ethyl-1-[4-(4-hydroxybenzoyl)-benzyl]-7-methylimidazo[1,2-a]pyrimidin-5(1H)-one (136 mg), 4-(2-chloroethyl)morpholine hydrochloride (154 mg) and potassium carbonate (205 mg) in DMF (7 ml) was stirred at 100° C. for 6 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, and dried. Then, hydrogen chloride/ethyl acetate was added and the precipitated hydrochloride was collected by filtration and dried to provide the title compound as colorless solid (132 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. additionThen, hydrogen chloride/ethyl acetate was added
  6. filtrationthe precipitated hydrochloride was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-b31b1e0fa2fa4489b49eec2d18fa26d4
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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