(1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide

Base Information

• Chemical Name: (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide
• CAS No.: 1449429-90-6
• Molecular Formula: C₂₂H₂₀BrFN₄O₂
• Molecular Weight: 471.329
• Mol file: 1449429-90-6.mol

Synonyms:(1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide

Chemical Property of (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide

There total 8 articles about (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide 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: 41.6%

(1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide (1369763-03-0) → (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide (1449429-90-6)

Guidance literature:

With bromine; In chloroform; at 0 - 20 ℃; for 96h;

DOI:10.1021/jm400772t

Reference yield:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one (63106-93-4,96847-52-8,96847-75-5,96847-53-9) → (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide (1449429-90-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

2.1: lipase acrylic resin from Candida antarctica / 17 h / 20 °C / Enzymatic reaction

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / 15 h / 0 - 20 °C

3.2: 1 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -60 - 20 °C

4.2: 14 h / 20 °C

5.1: ammonium chloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 168 h / 20 °C

6.1: potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 24 h / 80 °C

7.1: bromine / chloroform / 96 h / 0 - 20 °C

With sodium tetrahydroborate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxalyl dichloride; di-isopropyl azodicarboxylate; lipase acrylic resin from Candida antarctica; bromine; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 3.1: |Mitsunobu Displacement / 4.1: |Swern Oxidation;

DOI:10.1021/jm400772t

Reference yield:

(1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane (763126-74-5) → (1R,2S)-2-(((2-methyl-4-bromomethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide (1449429-90-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lipase acrylic resin from Candida antarctica / 17 h / 20 °C / Enzymatic reaction

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / 15 h / 0 - 20 °C

2.2: 1 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -60 - 20 °C

3.2: 14 h / 20 °C

4.1: ammonium chloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 168 h / 20 °C

5.1: potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 24 h / 80 °C

6.1: bromine / chloroform / 96 h / 0 - 20 °C

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxalyl dichloride; di-isopropyl azodicarboxylate; lipase acrylic resin from Candida antarctica; bromine; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; dichloromethane; chloroform; N,N-dimethyl-formamide; 2.1: |Mitsunobu Displacement / 3.1: |Swern Oxidation;

DOI:10.1021/jm400772t

upstream raw materials:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

(1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane

C₁₃H₁₆O₃

((1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-phenylcyclopropyl)methanol

Downstream raw materials:

(1R,2S)-2-(((2-methyl-4-hydroxymethylpyrimidin-5-yl)oxy)-methyl)-N-(5-fluoropyridin-2-yl)-2-phenylcyclopropanecarboxamide