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Process for preparing 8-bromo-7-(but-2-ynyl)-3-methyl-1-(4- methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione

IP.com Disclosure Number: IPCOM000210938D
Publication Date: 2011-Sep-18
Document File: 2 page(s) / 46K

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The IP.com Prior Art Database

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 67% of the total text.

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Process for preparing 8-bromo-7-(but-2-ynyl)-3-methyl-1-(4- methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione

8-Bromo-7-(but-2-ynyl)-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro- purine-2,6-dione of the following chemical structure:

N

O

N

N

Br

O

N

N N

It is an intermediate in a process for preparing 8-[3(R)-Aminopiperidin-1-yl]-7-(2- butynyl)-3-methyl-1-(4-methylquinazolin-2-ylmethyl)xanthine.

Provided is a process for preparing a crystalline form of 8-Bromo-7-(but-2-ynyl)-3- methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione:

N

N Cl

O

N

O

HN

N N

N

N

N

Br

Br

O

O

N

N N

3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine is mixed with equimolar 2-(chloromethyl)- 4-methylquinazoline in N-methylpyrrolidone in the presence of sodium carbonate. The reaction was monitored under heating during several hours in order to complete the process. The reaction mixture was cooled and mixed with aqueous ethanol. Acetic acid was added dropwise. The final mixture was cooled to the room temperature and stirred to increase precipitation. The precipitate was filtered, washed with ethanol and water. The solid was dried in oven at 60°C to afford crude 8-bromo-7-(but-2-ynyl)-3-methyl- 1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione. It was purified by isopropanol at reflux. The precipitate was filtered and dried in oven at 60°C to afford pure 8-bromo-7-(but-2-ynyl)-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-


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dihydro-purin...