Dimethyl Sulfate → 3-bromo-7-methyl-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine

HRID 523110Notes

Reaction equation

[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[N:4][N:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([CH3:11])[CH2:10][C:5]2=[N:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 3-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (Preparation 154, 29 mg, 0.143 mmol), K2CO3 (23.7 mg, 0.171 mmol), dimethyl sulfate (14 uL, 0.143 mmol in THF (3 mL) was stirred at 80° C. under microwave irradiation for 60 minutes. The reaction mixture was filtered and purified by elution through an SCX-2 column using 2M NH3/MeOH to give the title compound as yellow oil (16.5 mg, 53%).

Workup

filtrationThe reaction mixture was filtered
custompurified by elution through an SCX-2 column

Sources & evidence

ORD record: ord-f3054b6f8942464881b582b6fa53bccc
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334286B2

Reaction notes

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