N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine

Base Information

• Chemical Name: N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine
• CAS No.: 1421372-48-6
• Molecular Formula: C₂₆H₃₃N₇O
• Molecular Weight: 459.594

Synonyms:N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine

Chemical Property of N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine

Chemical Property:

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Technology Process of N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine

There total 8 articles about N¹-(2-dimethylaminoethyl)-5-methoxy-N¹-methyl-N⁴-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

N1-(2-(dimethylamino)ethyl)-N1-methyl-N4- [4- (1-methyl-1H-indol-3-yl)-5-methylpyrimidine-2-yl] -2-nitro 5-methoxy-benzene-1,4-diamine (1421372-49-7) → N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-N4-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine (1421372-48-6)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; for 3h; Reflux;

Reference yield:

3-(2-chloro-5-methylpyrimidin-4-yl)-1H-indole (945016-62-6) → N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-N4-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine (1421372-48-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / 24 h / 125 °C

3.1: N,N-dimethyl acetamide / 0.5 h / 140 °C / Microwave irradiation

4.1: iron; ammonium chloride / water; ethanol / 3 h / Reflux

With iron; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; mineral oil;

Reference yield:

2,6-dichloro-5-methylpyrimidine (1780-31-0) → N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-N4-[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,2,4-triamine (1421372-48-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: methylmagnesium bromide / tetrahydrofuran; 2-methyltetrahydrofuran / 0.67 h / 0 - 2 °C

1.2: 22 h / 20 - 60 °C / Cooling with ice

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 - 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / 24 h / 125 °C

4.1: N,N-dimethyl acetamide / 0.5 h / 140 °C / Microwave irradiation

5.1: iron; ammonium chloride / water; ethanol / 3 h / Reflux

With methylmagnesium bromide; iron; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; mineral oil;

upstream raw materials:

3-(2-chloro-5-methylpyrimidin-4-yl)-1H-indole

4-fluoro-2-methoxy-5-nitro-phenylamine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)-5-methylpyrimidine-2-amine

3-(2-chloro-5-methylpyrimidin-4-yl)-1-methyl-1H-indole

Downstream raw materials:

N-[2-(2-dimethylaminoethylmethylamino)-4-methoxy-5-[[5-methyl-4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide

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