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Potassium Carbonate → 7-[4-(6-Chloronicotinoyl)benzyloxy]-3,6-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 1291425
Notes
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Reaction equation

HRID 1291425 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:13])[C:8]([CH3:12])=[C:9]([OH:11])[N:10]=[C:5]2[S:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1>CN(C=O)C>[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31][O:11][C:9]3[N:10]=[C:5]4[S:4][CH:3]=[C:2]([CH3:1])[N:6]4[C:7](=[O:13])[C:8]=3[CH3:12])=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189188004-(6-Chloronicotinoyl)benzyl bromideHCID 1356675853,6-dimethyl-7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 189191357-[4-(6-Chloronicotinoyl)benzyloxy]-3,6-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-oneYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dimethyl-7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one (526 mg) and potassium carbonate (574 mg) in DMF (10 ml) was added 4-(6-chloronicotinoyl)benzyl bromide (852 mg) and the mixture was stirred at 80° C. for 2 hours. This reaction mixture was concentrated and the residue was diluted with water-ethyl acetate and extracted with ethyl acetate. The extract was purified by silica gel column chromatography (hexane: ethyl acetate =2:1) and recrystallized from ethyl acetate to provide the title compound as colorless solid (300 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. additionthe residue was diluted with water-ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customThe extract was purified by silica gel column chromatography (hexane: ethyl acetate =2:1)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eaf867a15216472db6aaba4109162e96
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753664

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes