(S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Base Information

• Chemical Name: (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine
• CAS No.: 1215865-28-3
• Molecular Formula: C₂₆H₂₆N₄O₃
• Molecular Weight: 442.517
• Mol file: 1215865-28-3.mol

Synonyms:

Chemical Property of (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

There total 11 articles about (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine 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: 22.0%

(S)-2-amino-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol (1215864-73-5) + Cyclohexylmethyl bromide (2550-36-9) → (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine (1215865-28-3)

Guidance literature:

(S)-2-amino-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol; With caesium carbonate; potassium iodide; In N,N-dimethyl-formamide; for 0.166667h; Sonication;

Cyclohexylmethyl bromide; In N,N-dimethyl-formamide; at 20 - 60 ℃;

DOI:10.1021/jm501266w

Reference yield:

2-bromo-5-methoxy-benzoic acid (22921-68-2) → (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine (1215865-28-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: caesium carbonate; copper(I) trifluoromethanesulfonate toluene adduct (1/1) / toluene; ethyl acetate / 16.08 h / 20 - 110 °C

2.1: sulfuric acid / 1.5 h / 60 °C

3.1: tetrahydrofuran; diethyl ether / 1.33 h / 0 - 20 °C

4.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / Reflux

5.1: iodine / tetrahydrofuran / 1 h / -20 - -15 °C

5.2: 1.67 h / 0 °C

6.1: diethylamine; carbon dioxide / isopropyl alcohol / Resolution of racemate

7.1: boron tribromide / dichloromethane / 1 h / 0 - 10 °C

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / 3 h / 100 °C / Sealed tube; Inert atmosphere

9.1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 0.17 h / Sonication

9.2: 20 - 60 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) trifluoromethanesulfonate toluene adduct (1/1); carbon dioxide; sulfuric acid; iodine; pyridinium p-toluenesulfonate; boron tribromide; potassium carbonate; caesium carbonate; diethylamine; potassium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jm501266w

Reference yield:

2-(4-bromophenoxy)-5-methoxybenzoic acid (1215864-17-7) → (S)-2'-(cyclohexylmethoxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine (1215865-28-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sulfuric acid / 1.5 h / 60 °C

2.1: tetrahydrofuran; diethyl ether / 1.33 h / 0 - 20 °C

3.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / Reflux

4.1: iodine / tetrahydrofuran / 1 h / -20 - -15 °C

4.2: 1.67 h / 0 °C

5.1: diethylamine; carbon dioxide / isopropyl alcohol / Resolution of racemate

6.1: boron tribromide / dichloromethane / 1 h / 0 - 10 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / 3 h / 100 °C / Sealed tube; Inert atmosphere

8.1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 0.17 h / Sonication

8.2: 20 - 60 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon dioxide; sulfuric acid; iodine; pyridinium p-toluenesulfonate; boron tribromide; potassium carbonate; caesium carbonate; diethylamine; potassium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm501266w

upstream raw materials:

2-bromo-7-methoxy-9H-xanthen-9-one

(S)-2-amino-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol

Cyclohexylmethyl bromide

2-bromo-5-methoxy-benzoic acid