Potassium Carbonate → 3,5-Dimethyl-2-[4-[4-(2-piperidinoethoxy)benzoyl]-benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one hydrochloride

HRID 1291350Notes

Reaction equation

HRID 1291350 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:12])=[CH:10][S:11][C:5]=2[N:4]=[C:3]1[S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.Cl.[Cl:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:31].[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:12])=[CH:10][S:11][C:5]=2[N:4]=[C:3]1[S:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[O:29])[C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:26][CH:27]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 189188093,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 189191603,5-Dimethyl-2-[4-[4-(2-piperidinoethoxy)benzoyl]-benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one hydrochlorideYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one (255 mg), 1-(2-chloroethyl)piperidine hydrochloride (122 mg) and potassium carbonate (250 mg) in DMF (8 ml) was stirred at 60° C. for 15 hours. This reaction mixture was concentrated, the residue was dissolved in ethyl acetate, and the solution was washed with water and dried. Then, HCl/ethyl acetate was added and the precipitated hydrochloride was collected by filtration and dried to provide the title compound as colorless solid (268 mg).

Workup

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

Sources & evidence

ORD record
ord-94b64c856fe94438baf8da1b00e709ec
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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