5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

Base Information

• Chemical Name: 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid
• CAS No.: 1296273-67-0
• Molecular Formula: C₃₂H₃₃N₃O₄
• Molecular Weight: 523.632

Synonyms:5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

Chemical Property of 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

There total 10 articles about 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid 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:

tert-butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate (1296273-65-8) → 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid (1296273-67-0)

Guidance literature:

tert-butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate; With water; sodium hydroxide; In tetrahydrofuran; methanol; at 50 ℃; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; methanol; water; at 20 ℃;

Reference yield:

tert-butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-hydroxypyrimidine-4-carboxylate (1192163-99-7) → 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid (1296273-67-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 0.5 h / -78 °C

2.1: potassium carbonate; silver(l) oxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C

4.1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene / 3 h / Inert atmosphere; Reflux

5.1: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.25 h / 50 °C

6.2: 20 °C

With hydrogenchloride; water; potassium carbonate; triethylamine; sodium hydroxide; silver(l) oxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene;

Reference yield:

4-tert-butyl 1-methyl 2-(benzyloxy)-3-oxosuccinate (1192164-00-3) → 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid (1296273-67-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium methylate / methanol / 14.5 h / 20 °C

2.1: triethylamine / dichloromethane / 0.5 h / -78 °C

3.1: potassium carbonate; silver(l) oxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

4.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C

5.1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene / 3 h / Inert atmosphere; Reflux

6.1: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.25 h / 50 °C

7.2: 20 °C

With hydrogenchloride; water; sodium methylate; potassium carbonate; triethylamine; sodium hydroxide; silver(l) oxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene;

upstream raw materials:

tert-butyl 5-(benzyloxy)-2-{(1-[4'-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

tert-butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

methyl 2-(benzyloxy)acetate

<4-(4-bromophenyl)phenyl>methanol

Downstream raw materials:

ethyl ({[5-(benzyloxy)-2-({1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate

({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid

({[2-{(1-[4'-(acetoxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid

4-{[2-(benzyloxy)-2-oxoethyl]carbamoyl}-2-{[1-(4'-{[(2,2-dimethylpropanoyl)oxy]methyl}biphenyl-4-yl)piperidin-4-yl]methyl}-6-methylpyrimidin-5-yl pivalate

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