Related Experiment Video
Updated: Apr 20, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
Development of an efficient route to CF3-substituted pyrrolopyrimidines through understanding the competition between
V M Tkachuk1, V A Sukach, K V Kovalchuk
1Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya str. 5, Kyiv, 02660, Ukraine. vsukach@gmail.com.
Abstract:
The regioselective base-catalyzed addition of nitromethane to 2-oxo-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylates is reported. It was found that the Michael-like pathway is highly reversible and substantially dominating under conditions of kinetic control (0-5 °C, 10 h) whereas the aza-Henry reaction leads to thermodynamically stable adducts after 8-24 h exposure at room temperature. The adjacent nitro and alkoxycarbonyl groups were exploited to demonstrate the synthetic potential of the obtained products by converting to the isomeric trifluoromethylated pyrrolo[3,4-d]pyrimidine-2,5-diones. With this aim an efficient protocol for selective reduction of nitro-derivatives to the corresponding 4- or 6-aminomethyl-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates and their subsequent thermal cyclocondensations was applied.
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Nucleophilic Aromatic Substitution: Elimination–Addition
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

