Methyl chloroacetate → 2-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 868950Notes

Reaction equation

HRID 868950 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N:15]1[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([CH3:22])[C:16]1=[NH2+:23].[OH-].[Na+].[Cl:26][CH2:27][C:28](OC)=O>C(O)C>[Cl:26][CH2:27][C:28]1[N:23]=[C:16]2[C:17]([CH3:22])=[N:18][CH:19]=[C:20]([CH3:21])[N:15]2[N:14]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 14798Sodium HydroxideHCID 178425979HCID 178425979, compound

Product 1

HCID 591512352-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazineYield 36.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-amino-3,6-dimethylpyrazin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate (2.0 g, 5.9 mmol) and sodium hydroxide (480 mg, 12 mmol) in ethanol (20 mL) was stirred at 60° C. for 1 h; methyl 2-chloroacetate (1.34 g, 12.4 mmol) was then added slowly. The reaction mixture heated at reflux for 4 h, then the solvent was removed. The product was purified by column chromatography to give 2-(chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine as a yellow solid (420 mg). MS (ESI): m/z 197 [M+H]+.

Workup

  1. temperatureThe reaction mixture heated
  2. temperatureat reflux for 4 h
  3. customthe solvent was removed
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-c343a53274a542e58b8267d1459ac418
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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