7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Base Information

• Chemical Name: 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine
• CAS No.: 1339892-19-1
• Molecular Formula: C₂₁H₂₂N₆
• Molecular Weight: 358.446
• Mol file: 1339892-19-1.mol

Synonyms:7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Chemical Property of 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

There total 8 articles about 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine 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: 23.55%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 5-chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine (1339892-17-9) → 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (1339892-19-1)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 100 ℃; for 18h; Inert atmosphere;

Reference yield:

tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate (769944-78-7) → 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (1339892-19-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) / 1,4-dioxane / 1.5 h / 110 °C / Inert atmosphere

2.1: potassium phosphate; water / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / isopropyl alcohol / 54 h / 90 °C / Inert atmosphere

2.3: pH 9

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

4.1: sodium tris(acetoxy)borohydride / ISOPROPYLAMIDE; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.1: N,N-diethylaniline; trichlorophosphate / 4 h / 50 °C / Inert atmosphere

5.2: Cooling with ice

6.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 18 h / 100 °C / Inert atmosphere

With potassium phosphate; water; sodium tris(acetoxy)borohydride; potassium carbonate; triethylamine; trifluoroacetic acid; N,N-diethylaniline; trichlorophosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; ISOPROPYLAMIDE; water; isopropyl alcohol;

Reference yield:

4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (956136-85-9) → 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (1339892-19-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium phosphate; water / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / isopropyl alcohol / 54 h / 90 °C / Inert atmosphere

1.3: pH 9

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3.1: sodium tris(acetoxy)borohydride / ISOPROPYLAMIDE; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.1: N,N-diethylaniline; trichlorophosphate / 4 h / 50 °C / Inert atmosphere

4.2: Cooling with ice

5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 18 h / 100 °C / Inert atmosphere

With potassium phosphate; water; sodium tris(acetoxy)borohydride; potassium carbonate; trifluoroacetic acid; N,N-diethylaniline; trichlorophosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; ISOPROPYLAMIDE; water; isopropyl alcohol;

upstream raw materials:

pyrazole-4-boronic acid pinacol ester

5-chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine

tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate

4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

3-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile