Potassium Carbonate → 2-[4-(6-Chloronicotinoyl]benzylthio]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1291389Notes

Reaction equation

HRID 1291389 reaction equation
[SH: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].[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][S:1][C:2]3[N:3]=[C:4]4[CH:13]=[CH:12][CH:11]=[CH:10][N:5]4[C:6](=[O:9])[C:7]=3[CH3:8])=[CH:23][CH:22]=2)=[O:20])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189188004-(6-Chloronicotinoyl)benzyl bromideHCID 189188982-mercapto-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 189190212-[4-(6-Chloronicotinoyl]benzylthio]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-mercapto-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (599 mg), 4-(6-chloronicotinoyl)benzyl bromide (1.179 g) and potassium carbonate (1.148 g) in DMF (40 ml) was stirred at room temperature for 2 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was recrystallized from tetrahydrofuranethyl acetate to provide the title compound as colorless solid (367 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 recrystallized from tetrahydrofuranethyl acetate

Sources & evidence

ORD record
ord-1669beb0124e47aa9e44218fbdbd47f5
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…