(S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Base Information

• Chemical Name: (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one
• CAS No.: 1605328-72-0
• Molecular Formula: C₁₉H₁₈BrN₇O
• Molecular Weight: 440.302

Synonyms:(S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Chemical Property of (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Chemical Property:

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Technology Process of (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

There total 8 articles about (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one 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: 60.0%

(S)-2-(1-aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1403943-08-7) + 5-bromo-6-chloro-pyrimidin-4-ylamine (663193-80-4) → (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1605328-72-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; cesium fluoride; In tert-butyl alcohol; at 140 ℃; for 40h; Sealed tube;

Reference yield:

methyl 3-methyl-1H-pyrrole-2-carboxylate (40611-69-6) → (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1605328-72-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide / methanol / 60 °C

2.1: oxalyl dichloride / dichloromethane / 3 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

4.1: sodium hydroxide; ammonium chloride; ammonium hydroxide; sodium hypochlorite / diethyl ether; tert-butyl methyl ether / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 0 - 20 °C

6.1: triethylamine; triphenylphosphine; bromine / dichloromethane / 2 h / 60 °C

6.2: 32 h / 100 °C

7.1: trifluoroacetic acid / dichloromethane / 20 °C

8.1: N-ethyl-N,N-diisopropylamine; cesium fluoride / tert-butyl alcohol / 40 h / 140 °C / Sealed tube

With ammonium hydroxide; sodium hypochlorite; oxalyl dichloride; bromine; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; sodium hydroxide; In methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; ethyl acetate; tert-butyl alcohol;

Reference yield:

3-methyl-1H-pyrrole-2-carboxylic acid (90724-57-5) → (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1605328-72-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: oxalyl dichloride / dichloromethane / 3 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

3.1: sodium hydroxide; ammonium chloride; ammonium hydroxide; sodium hypochlorite / diethyl ether; tert-butyl methyl ether / 20 °C

4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 0 - 20 °C

5.1: triethylamine; triphenylphosphine; bromine / dichloromethane / 2 h / 60 °C

5.2: 32 h / 100 °C

6.1: trifluoroacetic acid / dichloromethane / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; cesium fluoride / tert-butyl alcohol / 40 h / 140 °C / Sealed tube

With ammonium hydroxide; sodium hypochlorite; oxalyl dichloride; bromine; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; sodium hydroxide; In diethyl ether; dichloromethane; tert-butyl methyl ether; ethyl acetate; tert-butyl alcohol;

upstream raw materials:

(S)-2-(1-aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

5-bromo-6-chloro-pyrimidin-4-ylamine

methyl 3-methyl-1H-pyrrole-2-carboxylate

3-methyl-1H-pyrrole-2-carboxylic acid

Downstream raw materials:

(S)-N-(5-(4-amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-2-methoxypyridin-3-yl)-4-hydroxybenzamide

(S)-N-(3-(4-amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-methoxyphenyl)butane-1-sulfonamide

(S)-2-(1-((6-amino-5-(5-(difluoromethoxy)pyridin-3-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

(S)-2-(1-((6-amino-5-(3-(difluoromethyl)-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

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