2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1297931-18-0
• Molecular Formula: C₂₇H₃₂FN₅O₄
• Molecular Weight: 509.581
• Mol file: 1297931-18-0.mol

Synonyms:2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 6 articles about 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 26.0%

meta-fluoroaniline (372-19-0) + 2-(S)-{[2-chloro-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1297931-02-2) → 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1297931-18-0)

Guidance literature:

With potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 180 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

Reference yield:

4-methoxy-phenol (150-76-5) → 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1297931-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate / water; acetone / 0 - 20 °C

2: acetic acid; iron / methanol / 2.5 h / 65 °C

3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

4: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 0.5 h / 180 °C / Inert atmosphere; Microwave irradiation

With sodium tris(acetoxy)borohydride; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In methanol; water; 1,2-dichloro-ethane; acetone; toluene;

Reference yield:

{2-[2,4-Bis-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]ethyl}-carbamic acid tert-butyl ester (1297930-95-0) → 2-(S)-{[2-(3-fluoro-phenylamino)-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1297931-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 20 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 72 h / 20 °C

3: potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 0.5 h / 180 °C / Inert atmosphere; Microwave irradiation

With potassium carbonate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dichloromethane; toluene; acetonitrile;

upstream raw materials:

4-methoxy-phenol

meta-fluoroaniline

2-(S)-{[2-chloro-4-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

{2-[2,4-Bis-(4-methoxy-phenoxy)-pyrimidin-5-ylamino]ethyl}-carbamic acid tert-butyl ester