Sodium Iodide → 7-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]-1,1-dioxo-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione

HRID 357077Notes

Reaction equation

HRID 357077 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:29](=[O:30])[C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:21]2[S:22](=[O:27])(=[O:26])[CH2:23][CH2:24][CH2:25][N:20]2[C:19]1=[O:37].[I-].[Na+]>CN(C)C=O.O>[N:12]1[CH:11]=[CH:10][N:9]2[C:4]([S:3][CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:29](=[O:30])[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:21]4[S:22](=[O:27])(=[O:26])[CH2:23][CH2:24][CH2:25][N:20]4[C:19]3=[O:37])=[CH:5][CH:6]=[CH:7][C:8]=12

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 189367797-(4-chlorobutyl)-1,1-dioxo-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]-thiazine-6,8(7H)-dioneHCID 178418687HCID 178418687, compound

Product 1

HCID 189366337-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]-1,1-dioxo-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.24 g (6.0 mmol) of 60% oily sodium hydride in 40 ml of N,N-dimethylformamide, 0.98 g (6.0 mmol) of 5-mercaptoimidazo[1,2-a]pyridine was added at room temperature, followed by stirring for 10 minutes. To this mixture, 2.87 g (5.97 mmol) of 7-(4-chlorobutyl)-1,1-dioxo-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]-thiazine-6,8(7H)-dione and 0.90 g (6.0 mmol) of sodium iodide were added, followed by stirring at 80° C. for 3 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate 3 times. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1) to yield 1.26 g (43.7%, white foamy substance) of the desired product.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at 80° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate 3 times
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-dfd545c5577e423285e7dd1c4eed9679
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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