4-chloro-N,6-dimethyl-1,3,5-triazin-2-amine synthesis

Yield:57639-19-7 31.41 g

Reaction Conditions:

in tetrahydrofuran;dichloromethane;water; for 5 h;Solvent;

Steps:

Synthesis of 4-chloro-N,6-dimethyl-1,3,5-triazin-2-amine(6)

To a stirred solution of 2,4,6-trichloro-1,3,5-triazine 4 (50 g,0.27 mol) in DCM (500 mL) was dropped with a solution of3 M methylmagnesium bromide in THF (100 mL, 0.30 mol)at - 10 °C under a N2atmosphere. The resulting mixturewas kept at this temperature for 3 h. The 30% methylamineaqueous solution (33.36 mL, 0.30 mol) was added and theresulted mixture continued to stir for 5 h. When the reactioncompleted, the reaction mixture was quenched with water(3 × 50 mL). Then organic layer was washed with brine(100 mL), dried over Na2SO4and filtered. The filtrate wasconcentrated in vacuo to obtain intermediate 6 (31.41 g,0.20 mol, 73.2%) as white solid; m.p:140-141 .1H NMR (600 MHz, DMSO-d6) δ 8.42 (s, 1H), 2.83 (d,J = 4.8 Hz, 3H), 2.33 (s, 3H); 13C NMR (151 MHz, DMSOd6)δ 177.9, 169.9, 166.3, 27.8, 25.5.LCMS [M + H]+m/z calcd 159.04, found 158.98.

References:

Duan, Meibo;Fu, Siyu;Han, Yu;Tian, Ye;Jiang, Jia;Xing, Yongpeng;Hou, Yunlei;Zhao, Yanfang [Chemical Papers,2022,vol. 76,# 5,p. 2883 - 2891]