1-Phenylpiperazine → 3-Methyl-2-[4-[4-(4-phenylpiperazinylmethyl)benzoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1291346Notes

Reaction equation

HRID 1291346 reaction equation
[SH:1][C:2]1[N:3]([CH3:12])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.Br[CH2:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1.[CH:31]1[CH:32]=[CH:33][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:35][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][N:3]1[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]1[S:1][CH2:14][C:15]1[CH:30]=[CH:29][C:18]([C:19](=[O:20])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:40]3[CH2:41][CH2:42][N:37]([C:34]4[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=4)[CH2:38][CH2:39]3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 178481668HCID 178481668, compound

Product 1

HCID 189192423-Methyl-2-[4-[4-(4-phenylpiperazinylmethyl)benzoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-oneYield 15.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-mercapto-3-methylthieno[3,2-d]-pyrimidin-4(3H)-one (990 mg), 4,4'-bis (bromomethyl)benzophenone (1.75 g), phenylpiperazine (810 mg) and potassium carbonate (828 mg) in DMF (30 ml) was stirred at 60° C. for 2 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was washed with water, dried, and concentrated, and the residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=250:1:0.1) to provide the title compound as light-yellow syrup (428 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. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=250:1:0.1)

Sources & evidence

ORD record
ord-da82c456386f405c9142af27998083c0
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…