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

Base Information

• Chemical Name: ({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid
• CAS No.: 1296273-07-8
• Molecular Formula: C₂₇H₃₀N₄O₅
• Molecular Weight: 490.559
• Mol file: 1296273-07-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about ({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic 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: 82.0%

ethyl ({[5-hydroxy-2-({1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (1296273-68-1) → ({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid (1296273-07-8)

Guidance literature:

ethyl ({[5-hydroxy-2-({1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate; With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; methanol; water;

Reference yield:

<4-(4-bromophenyl)phenyl>methanol (84337-86-0) → ({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid (1296273-07-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

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

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

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

4.2: 20 °C

5.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / tetrahydrofuran; methanol / 14 h / 20 °C

6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 2.5 h / 20 °C

7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.5 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; water; hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium hydroxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; ethyl acetate; toluene;

Reference yield:

tert-butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-hydroxypyrimidine-4-carboxylate (1192163-99-7) → ({[5-hydroxy-2-({1-[4’-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid (1296273-07-8)

Guidance literature:

Multi-step reaction with 9 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

7.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / tetrahydrofuran; methanol / 14 h / 20 °C

8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 2.5 h / 20 °C

9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.5 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; water; hydrogen; potassium carbonate; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium hydroxide; silver(l) oxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene;

upstream raw materials:

<4-(4-bromophenyl)phenyl>methanol

tert-butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-hydroxypyrimidine-4-carboxylate

tert-butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-{[(trifluoromethyl)sulfonyl]oxy}pyrimidine-4-carboxylate

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

Downstream raw materials:

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

({[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