Methyl iodide → 2-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

HRID 2239832Notes

Reaction equation

HRID 2239832 reaction equation
[OH-].[Na+].[S:3]=[C:4]1[NH:9][C:8](=[O:10])[N:7]2[N:11]=[CH:12][CH:13]=[C:6]2[NH:5]1.[CH3:14]I>CCO>[CH3:14][S:3][C:4]1[NH:9][C:8](=[O:10])[N:7]2[N:11]=[CH:12][CH:13]=[C:6]2[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178518767HCID 178518767, compound

Product 1

HCID 1354442592-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-oneYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.75N NaOH solution (39.52 mmol, 22.58 ml) was added to a suspension of 2-thioxo-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one (3.32 g, 19.76 mmol) from 1b in absolute EtOH (80 mL). Methyl iodide (2.80 g, 19.76 mmol) was then added and the reaction mixture was allowed to stir for 2 hours at room temperature. The resulting precipitate was collected by vacuum filtration, suspended in water (110 mL) and acidified with 2NH2SO4. The solution was stirred at 0° C. for 5 minutes and the new precipitate was collected by vacuum filtration, washed with cold water, and then air dried to give 1.88 g (52%) of 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one.

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. stirringThe solution was stirred at 0° C. for 5 minutes
  3. filtrationthe new precipitate was collected by vacuum filtration
  4. washwashed with cold water
  5. customair dried

Sources & evidence

ORD record
ord-3fb4928f67ae426898b4b3a0483597b7
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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