Chemistry
Heterocyclic Building Blocks
Pyrimidines
2-bromopyrimidine
Nucleophilic Substitution (SN2): The bromine atom in 2-bromopyrimidine is susceptible to nucleophilic substitution reactions, particularly SNSN2 reactions. Nucleophiles can attack the electrophilic carbon, leading to substitution of the bromine atom. Common nucleophiles include amines and organometallic reagents.
Cross-Coupling Reactions: 2-bromopyrimidine can participate in various cross-coupling reactions, such as Suzuki-Miyaura coupling or Stille coupling. These reactions involve the coupling of the bromine-substituted pyrimidine with another organic compound containing a compatible functional group under the influence of a catalyst.
Palladium-Catalyzed Reactions: Palladium-catalyzed reactions, such as Heck reactions or Sonogashira reactions, may be applicable to 2-bromopyrimidine. These reactions involve coupling with olefins or alkynes, respectively, in the presence of a palladium catalyst.
Reductive Coupling: The bromine atom can be replaced by hydrogen through reductive coupling reactions, often using metal catalysts like palladium on carbon (Pd/C) or Raney nickel.
Amidation Reactions: 2-Bromopyrimidine can undergo amidation reactions with amines or amides, leading to the formation of substituted pyrimidine derivatives.
Suzuki Reaction: In the Suzuki reaction, 2-bromopyrimidine can react with boronic acids or boronate esters in the presence of a palladium catalyst to form a biaryl compound.
Halogen-Metal Exchange: The bromine atom can be exchanged with another halogen in the presence of a strong base, such as butyllithium or sodium amides.
Oxidative Coupling: Under certain conditions, 2-bromopyrimidine may undergo oxidative coupling reactions to form dimeric or oligomeric products.
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tert-Butyl (2-bromopyrimidin-5-yl)carbamate
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Ethyl 2-bromopyrimidine-5-carboxylate
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Methyl 2-bromopyrimidine-5-carboxylate
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tert-Butyl (2-bromopyrimidin-4-yl)carbamate