Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides

A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides <strong>10</strong>{<em>1</em>,<em>2</em>; <em>1–12</em>} was prepared by a parallel solution-phase approach. The...

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Main Authors: Branko Stanovnik, Uroš Grošelj, Jurij Svete, Georg Dahmann, Drago Kočar, Jernej Baškovč, Bojana Črček
Format: Article
Language:English
Published: MDPI AG 2012-05-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/17/5/5363
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author Branko Stanovnik
Uroš Grošelj
Jurij Svete
Georg Dahmann
Drago Kočar
Jernej Baškovč
Bojana Črček
author_facet Branko Stanovnik
Uroš Grošelj
Jurij Svete
Georg Dahmann
Drago Kočar
Jernej Baškovč
Bojana Črček
author_sort Branko Stanovnik
collection DOAJ
description A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides <strong>10</strong>{<em>1</em>,<em>2</em>; <em>1–12</em>} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (<strong>11</strong>) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids <strong>17</strong>{<em>1</em>,<em>2</em>} followed by parallel amidation of <strong>17</strong>{<em>1</em>,<em>2</em>} with a series of 12 aliphatic amines <strong>18</strong>{<em>1–12</em>} to afford the corresponding carboxamides <strong>10</strong> in good overall yields and in 80–100% purity.
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spelling doaj.art-672e2da84c0a467c84d7183057b568592022-12-22T02:04:41ZengMDPI AGMolecules1420-30492012-05-011755363538410.3390/molecules17055363Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamidesBranko StanovnikUroš GrošeljJurij SveteGeorg DahmannDrago KočarJernej BaškovčBojana ČrčekA library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides <strong>10</strong>{<em>1</em>,<em>2</em>; <em>1–12</em>} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (<strong>11</strong>) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids <strong>17</strong>{<em>1</em>,<em>2</em>} followed by parallel amidation of <strong>17</strong>{<em>1</em>,<em>2</em>} with a series of 12 aliphatic amines <strong>18</strong>{<em>1–12</em>} to afford the corresponding carboxamides <strong>10</strong> in good overall yields and in 80–100% purity.http://www.mdpi.com/1420-3049/17/5/5363parallel synthesispyrimidines2-(heteroaryl)ethylamines
spellingShingle Branko Stanovnik
Uroš Grošelj
Jurij Svete
Georg Dahmann
Drago Kočar
Jernej Baškovč
Bojana Črček
Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
Molecules
parallel synthesis
pyrimidines
2-(heteroaryl)ethylamines
title Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
title_full Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
title_fullStr Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
title_full_unstemmed Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
title_short Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
title_sort parallel synthesis of 2 substituted 6 5 oxo 1 phenylpyrrolidin 3 yl pyrimidine 5 carboxamides
topic parallel synthesis
pyrimidines
2-(heteroaryl)ethylamines
url http://www.mdpi.com/1420-3049/17/5/5363
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