Tetrahydrofuran → HCID 54355857, compound

HRID 1460375Notes

Reaction equation

HRID 1460375 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12](=[O:28])(=[O:27])[NH:13][C:14]3[C:19]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:26])[N:11]=[C:4]2[N:3]=1.[H-].[Na+].O1CCC[CH2:32]1>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12](=[O:28])(=[O:27])[N:13]([CH3:32])[C:14]3[C:19]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:26])[N:11]=[C:4]2[N:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 54568158HCID 54568158, compound

Product 1

HCID 54355857HCID 54355857, compoundYield 71%

Procedure

1.5g of 5,7-dimethyl-2-(N-[2-chloro-6-(2-ethoxyethoxy)phenyl]-sulphamoyl)-1,2,4-triazolo[1,5-a]pyrimidine (prepared using the procedures described in Preparation Example 1, Variant A, were stirred in dry tetrahydrofuran under dry nitrogen at ambient temperature. To the pale yellow solution was added 60% sodium hydride and a white floccular solid formed over 60 minutes. The tetrahydrofuran was removed and the sodium salt resuspended in dry dimethyl formamide. 0.5g of methyl iodide was added and the mixture stirred under nitrogen overnight at ambient temperature. After concentration of the reaction mixture the residue was treated with water and extracted twice with 20ml of ethyl acetate. The organic phases were combined, dried over magnesium sulphate, filtered and concentrated. The crude product was then purified by flash chromatography to give 1.1g (71% yield) of 5,7-dimethyl-2-(N-methyl-N-[2-chloro-6-(2-ethoxyethoxy)phenyl]-sulphamoyl)-1,2,4-triazolo[1,5-a]pyrimidine (Compound No. 26) as a white solid.

Workup

  1. customdescribed in Preparation Example 1, Variant A
  2. customa white floccular solid formed over 60 minutes
  3. customThe tetrahydrofuran was removed
  4. addition0.5g of methyl iodide was added
  5. additionAfter concentration of the reaction mixture the residue was treated with water
  6. extractionextracted twice with 20ml of ethyl acetate
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was then purified by flash chromatography

Sources & evidence

ORD record
ord-b765aa80d979446e9ce1fcc2c99a98be
Source dataset
uspto-grants-1991_12
Patent number
US05071468

Reaction notes

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