6-chloro-N,N-dimethyl-1,3,5-triazine-2,4-diamine synthesis
- Product Name:6-chloro-N,N-dimethyl-1,3,5-triazine-2,4-diamine
- CAS Number:32998-04-2
- Molecular formula:C5H8ClN5
- Molecular Weight:173.6
933-20-0
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506-59-2
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32998-04-2
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Yield:32998-04-2 150 mg
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in tetrahydrofuran at 20; for 1 h;
Steps:
440
To a solution of 4,6-dichloro-1,3,5-triazin-2-amine 306a (300 mg, 2.72 mmol) in THF (5.0 mL) was added dimethylamine hydrochloride (220 mg, 1.00 mmol) and DIPEA (703 mg, 5.45 mmol). The reaction mixture was stirred at ambient temperature for 1 h and then quenched with water. The precipitate formed was collected by filtration, washed with water and dried to give 6-chloro-N2,N2-dimethyl-1,3,5-tnazine-2,4-diamine 306e (150 mg). The crude material was used in the next step without further purification. ESI+APCI MS m/z 174 [M + H ] + Compound 6-(4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[l,2-a]pyridin-7-yl)piperazin-1-yl)- N2,N2-dimethyl-1, 3,5-triazine-2,4-diamine 307e was prepared in the same manner as 4-chloro-6-(4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazin-1-yl)-1,3,5-triazin-2-amine 307a, and was obtained as an off-white solid (22% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.36 (d, J= 7.5 Hz, 1 H), 8.14(s, 1H), 8 ,05 (s, 1H), 6.90 - 6.88 (m, 21 1 ). 6.72 (s, 1H),6.25 (bs, 2H), 4.01 (s, 3H), 3.94 (s, 3H), 3.88 - 3.80 (m, 4H), 3.28 - 3.21 (rn, 4H), 3.02 (s, 6H). HPLC (Method 5) 99.69% (AUC), fR 12 39 min. ESI+APCI MS m/z 510 | .M + H ]
References:
WO2017/58503,2017,A1 Location in patent:Page/Page column 330; 333
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32998-04-2
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32998-04-2
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