Sodium Chloride → HCID 23032455, compound

HRID 917340Notes

Reaction equation

HRID 917340 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[N:11][CH:10]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 12933341(Pyrimidin-4-yl)methanol

Product 1

HCID 23032455HCID 23032455, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 4 g of N,N-dimethylformamide were dissolved 304 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 200 mg of 4-pyrimidylmethyl alcohol, 87 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 15 minutes. After stirring for 2 hours at room temperature, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 210 mg of 5-(4-pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (39)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringAfter stirring for 2 hours at room temperature
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-9a3da3627ea745b1bf273637f4429cc8
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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