1,2,4-Triazine, 3,6-dichloro-5-methyl- synthesis

Yield:132434-82-3 46 %

Reaction Conditions:

in tetrahydrofuran at -78;

Steps:

2.1 Step 1 :

A solution of 3,5,6-trichloro-l,2,4-triazine (2.0 g, 10.8 mmol) in dry THF (22 mL) was cooled to -78 °C and methylmagnesium bromide (1 mol/L in THF) (11 mL,l 1.4 mmol) was added dropwise. The reaction mixture was stirred at -78 °C for 5h and then was allowed to warm to rt slowly. Upon completion, the reaction was quenched with water and partitioned between water and ethyl acetate. The combined organic extracts were dried over Na2SO4, concentrated, purified by silica-gel column chromatography eluting with a gradient (0-20%) CfhCh/MeOH to afford 3,6-dichloro-5-methyl-l,2,4-triazine (819 mg, 46% yield) as a colorless oil. TH NMR (400 MHz, chloroform-t/) 6 2.72 (s, 3 H); material does not ionize on LCMS.

References:

WO2023/28536,2023,A1 Location in patent:Page/Page column 48; 49