N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine

Base Information

• Chemical Name: N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine
• CAS No.: 1606178-37-3
• Molecular Formula: C₂₁H₃₁BrN₄S
• Molecular Weight: 451.474

Synonyms:N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine

Chemical Property of N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine

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Technology Process of N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine

There total 5 articles about N⁴-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N⁶,N⁶-dipropylpyrimidine-4,6-diamine 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: 72.9%

N-(2-bromo-4-isopropylphenyl)-6-chloro-2-methyl-5-(methylthio)pyrimidin-4-amine (1606178-64-6) + di-n-propylamine (142-84-7) → N4-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N6,N6-dipropylpyrimidine-4,6-diamine (1606178-37-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos; at 100 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.03.040

Reference yield:

2-bromo-4-isopropylphenylisothiocyanate (246166-33-6) → N4-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N6,N6-dipropylpyrimidine-4,6-diamine (1606178-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; sulfur / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: Reflux; Inert atmosphere

3.1: sodium hydroxide / 100 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: trichlorophosphate / Inert atmosphere; Reflux

5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; sulfur; triethylamine; sodium hydroxide; XPhos; trichlorophosphate; In dimethyl sulfoxide; 1.1: |Gewald Aminoheterocycles Synthesis / 1.2: |Gewald Aminoheterocycles Synthesis;

DOI:10.1016/j.ejmech.2014.03.040

Reference yield:

4-amino-3-(2-bromo-4-isopropylphenyl)-2-thioxo-2,3-dihydrothiazole-5-carboxamide (228254-23-7) → N4-(2-bromo-4-isopropylphenyl)-2-methyl-5-(methylthio)-N6,N6-dipropylpyrimidine-4,6-diamine (1606178-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Reflux; Inert atmosphere

2.1: sodium hydroxide / 100 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: trichlorophosphate / Inert atmosphere; Reflux

4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; sodium hydroxide; XPhos; trichlorophosphate;

DOI:10.1016/j.ejmech.2014.03.040

upstream raw materials:

2-bromo-4-isopropylphenylisothiocyanate

N-(2-bromo-4-isopropylphenyl)-6-chloro-2-methyl-5-(methylthio)pyrimidin-4-amine

di-n-propylamine

4-amino-3-(2-bromo-4-isopropylphenyl)-2-thioxo-2,3-dihydrothiazole-5-carboxamide

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