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

Abstract

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.

Keywords

• parallel synthesis
• pyrimidines
• 2-(heteroaryl)ethylamines