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

HRID 1771997Notes

Reaction equation

[NH2:1][N:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]1=[NH2+:10].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[OH-].[Na+].[Cl:26][CH2:27][C:28](OC)=O>CCO>[Cl:26][CH2:27][C:28]1[N:10]=[C:3]2[C:4]([CH3:9])=[N:5][CH:6]=[C:7]([CH3:8])[N:2]2[N:1]=1

Participants

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 NaOH (480 mg, 12 mmol) in EtOH (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 was refluxed for 4 h, then the solvent was removed. The product was purified by silica gel column chromatography to give 2-(chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine as a yellow solid (420 mg, yield 36.3%). ESI MS: m/z 197 [M+1]+.

Workup

temperatureThe reaction mixture was refluxed for 4 h
customthe solvent was removed
customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-d7125943e5c745979c35f767be1f14a1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249162B2

Reaction notes

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