Sodium Chloride → 5-(2-Pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazole

HRID 917337Notes

Reaction equation

HRID 917337 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][CH:12]=[N:11][C:10]=1[CH2:15][OH:16].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:9]1[CH:14]=[CH:13][CH:12]=[N:11][C:10]=1[CH2:15][O:16][C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 27630242-Pyrimidinemethanol

Product 1

HCID 121513915-(2-Pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazoleYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 3.6 g of N,N-dimethylformamide were dissolved 304 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 200 mg of 2-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 1.5 hour 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 278 mg of 5-(2-pyrimidylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (36)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringAfter stirring for 1.5 hour 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-5ccab987ef8f4b57a70450fef65d22b5
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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