Linagliptin Impurity D

Base Information

• Chemical Name: Linagliptin Impurity D
• CAS No.: 666816-91-7
• Molecular Formula: C20H28N6O4
• Molecular Weight: 416.47400
• Mol file: 666816-91-7.mol

Synonyms:3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine;Linagliptin Impurity D;3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butyloxycarbonylamino)-piperidin-1-yl]-3,7-dihydro-1H-purine-2,6-dione;3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butyloxycarbonylamino)-piperidin-1-yl]-xanthine;3-methyl-7-(but-2-yn-1-yl)-8-[(R)-3-(tert-butyloxycarbonylamino)-piperidin-1-yl]-xanthine;3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine;Linagliptin Impurity 21;3-methyl-7-(2-butyn-1-yl)-8-(3-(R)-tert-butoxycarbonylaminopiperidin-1-yl)-xanthine;3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butyloxycarbonylamino)-piperidin-1-yl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine;Linagliptin impurity;Carbamic acid,[(3R)-1-[7-(2-butynyl)-2,3,6,7-tetrahydro-3-methyl-2,6-dioxo-1H-purin-8-yl]-3-piperidinyl]-, 1,1-dimethylethyl ester;Linagliptin;

Chemical Property of Linagliptin Impurity D

Chemical Property:

• PKA: 9.38±0.70(Predicted)
• PSA: 114.25000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 1.39600

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

3-Methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tertbutyloxycarbonylamino)piperidin-1-yl]-xanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tertbutyloxycarbonylamino)piperidin-1-yl]-xanthine is a useful synthetic compound.

Technology Process of Linagliptin Impurity D

There total 3 articles about Linagliptin Impurity D 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: 94.0%

(R)-piperidin-3-ylcarbamic acid tert-butyl ester (309956-78-3,172603-05-3) + 8-bromo-7-(but2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6–dione (666816-98-4) → 3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butoxycarbonylamino)piperidin-1-yl]xanthine (666816-91-7)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 114 ℃; for 6h;

Reference yield:

3-methyl-8-bromoxanthine (93703-24-3) → 3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butoxycarbonylamino)piperidin-1-yl]xanthine (666816-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; potassium iodide; methyl tributylammonium chloride / tetrahydrofuran / Inert atmosphere; Reflux

2: potassium iodide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / Isopropyl acetate / Reflux

With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; N-ethyl-N,N-diisopropylamine; methyl tributylammonium chloride; potassium iodide; In tetrahydrofuran; Isopropyl acetate;

Reference yield:

→ 3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butoxycarbonylamino)piperidin-1-yl]xanthine (666816-91-7)

Guidance literature:

upstream raw materials:

(R)-piperidin-3-ylcarbamic acid tert-butyl ester

8-bromo-7-(but2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6–dione

3-methyl-8-bromoxanthine

Downstream raw materials:

Linagliptin

Refernces

• 1、 -. "Xanthine derivatives, their preparation and use". Paragraph 0149-0151. . Retrieved 2017/02/28.
• 2、 -. "8-[3-AMINO-PIPERIDIN-1-YL]-XANTHINE, THE PRODUCTION THEREOF AND THE USE IN THE FORM OF A DPP INHIBITOR". Page/Page column 30-31. . Retrieved 2008/06/13.