Chemistry Heterocyclic building blocks Pyrimidines 4,5-dichloropyrimidine

4,5-dichloropyrimidine

These compounds have the same murcko framework: 4,5-dichloropyrimidine

Nucleophilic Substitution (SNAr): The electron-deficient nature of the pyrimidine ring makes it susceptible to nucleophilic substitution reactions. Nucleophiles, such as amines or thiols, can replace one or both of the chlorine atoms. This reaction is often used in the synthesis of substituted pyrimidines.
Cross-Coupling Reactions: 4,5-dichloropyrimidine can undergo cross-coupling reactions, such as Suzuki-Miyaura coupling or Stille coupling, where it reacts with suitable organometallic reagents to form carbon-carbon bonds. This is a common strategy in organic synthesis for the introduction of various substituents.
Amination Reactions: The chlorine atoms can be replaced by amine groups through nucleophilic substitution reactions, leading to the formation of 4,5-diaminopyrimidine derivatives.
Alkylation Reactions: Under suitable conditions, 4,5-dichloropyrimidine can undergo alkylation reactions with alkyl halides or alkyl sulfonates, leading to the introduction of alkyl groups onto the pyrimidine ring.
Reductive Dehalogenation: Under certain conditions, 4,5-dichloropyrimidine can undergo reductive dehalogenation reactions, where one or both of the chlorine atoms are replaced with hydrogen atoms.
Cycloaddition Reactions: Depending on the reaction conditions, 4,5-dichloropyrimidine may participate in cycloaddition reactions, especially if there are suitable π-systems or double bonds present.

Further Reading:

Framework+−

(r)-7-(tetrahydrofuran-2-yl)-7h-pyrrolo[2,3-d]pyrimidine (r)-n-(piperidin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine 1,4,5,6-tetrahydropyrimidine 1-(3-fluorotetrahydrofuran-2-yl)pyrimidin-2(1h)-one 1-(5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione 1-(pyrimidin-2-yl)ethan-1-one 1-(pyrimidin-4-yl)ethan-1-one 1-(tetrahydrofuran-2-yl)pyrimidin-2(1h)-one 1h-pyrazolo[3,4-d]pyrimidin-4-amine 1h-pyrazolo[4,3-d]pyrimidine 2,4,5-trichloropyrimidine 2,4,6-trichloropyrimidine 2,4,6-triphenylpyrimidine 2,4-dichloro-6-methylpyrimidine 2,4-dichloropyrimidin-5-amine 2,4-dimethoxypyrimidine 2,4-dimethylpyrimidine 2-(1h-pyrazol-1-yl)pyrimidine 2-(chloromethyl)pyrimidine 2-(methylsulfonyl)pyrimidine 2-(methylthio)pyrimidin-4-amine 2-(methylthio)pyrimidine 2-(piperazin-1-yl)pyrimidine 2-(piperidin-1-yl)pyrimidine 2-(propylthio)pyrimidine 2-(pyridin-2-yl)pyrimidine 2-(pyrrolidin-1-yl)pyrimidine 2-(trifluoromethyl)pyrimidine 2-aminopyrimidin-4(3h)-one 2-bromopyrimidine 2-chloro-4-(trifluoromethyl)pyrimidine 2-chloro-4-methoxypyrimidine 2-chloro-4-methylpyrimidine 2-chloro-4-phenylpyrimidine 2-chloro-5-fluoropyrimidine 2-chloro-5-methylpyrimidine 2-chloro-5-nitropyrimidine 2-chloro-7h-pyrrolo[2,3-d]pyrimidine 2-chloropyrimidin-4-amine 2-cyclopropylpyrimidine 2-ethoxypyrimidine 2-ethylpyrimidine 2-fluoropyrimidine 2-hydrazineylpyrimidine 2-iodopyrimidine 2-methoxypyrimidin-4-amine 2-methoxypyrimidine 2-methylpyrimidin-4-amine 2-methylpyrimidin-4-ol 2-phenoxypyrimidine 2-phenylpyrimidin-5-amine 3-methylpyrimidin-4(3h)-one 4,5-dichloropyrimidine 4,6-dichloro-2-(methylthio)pyrimidine 4,6-dichloro-2-methylpyrimidine 4,6-dichloropyrimidin-2-amine 4,6-dichloropyrimidine 4,6-diphenylpyrimidine 4-(dimethoxymethyl)pyrimidine 4-(piperazin-1-yl)pyrimidine 4-(piperidin-1-yl)pyrimidine 4-(pyridin-3-yl)pyrimidine 4-(pyrimidin-2-yl)morpholine 4-(pyrimidin-4-yl)morpholine 4-(trifluoromethyl)pyrimidin-2-amine 4-(trifluoromethyl)pyrimidine 4-amino-1-(tetrahydrofuran-2-yl)pyrimidin-2(1h)-one 4-bromopyrimidine 4-chloro-2-(methylthio)pyrimidine 4-chloro-2-methoxypyrimidine 4-chloro-2-phenylpyrimidine 4-chloro-5-fluoro-2-methylpyrimidine 4-chloro-5-iodopyrimidine 4-chloro-5-methoxypyrimidine 4-chloro-5-methylpyrimidine 4-chloro-6-methoxypyrimidine 4-chloropyrimidin-2-amine 4-chloropyrimidin-5-amine 4-chloropyrimidine-5-carbonitrile 4-ethoxypyrimidine 4-fluoropyrimidine 4-iodopyrimidine 4-methoxy-2-methylpyrimidine 4-methoxypyrimidin-2-amine 4-methoxypyrimidine 4-methyl-2-(methylthio)pyrimidine 4-methylpyrimidin-2-amine 4-methylpyrimidine 4-phenoxypyrimidine 4-phenylpyrimidin-2-amine 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 5-(benzyloxy)pyrimidine 5-benzylpyrimidine 5-bromo-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione 5-bromo-2-(methylthio)pyrimidine 5-bromo-2-chloropyrimidine 5-bromo-2-methylpyrimidine 5-bromo-4-chloropyrimidine 5-bromo-7h-pyrrolo[2,3-d]pyrimidine 5-bromopyrimidin-4(3h)-one 5-chloropyrimidin-4(3h)-one 5-chloropyrimidine 5-chloropyrimidine-2,4(1h,3h)-dione 5-ethylpyrimidine 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidin-2(1h)-one 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione 5-fluoropyrimidin-4(3h)-one 5-fluoropyrimidine 5-fluoropyrimidine-2,4(1h,3h)-dione 5-iodo-7h-pyrrolo[2,3-d]pyrimidine 5-iodopyrimidine 5-methylpyrimidine 5-phenylpyrimidine 5h-pyrrolo[3,2-d]pyrimidine 6,7-dihydro-5h-cyclopenta[d]pyrimidine 6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidine 6-chloro-1h-pyrazolo[3,4-d]pyrimidine 6-chloropyrimidin-4-amine 7-(phenylsulfonyl)-7h-pyrrolo[2,3-d]pyrimidine 7h-pyrrolo[2,3-d]pyrimidin-2-amine 7h-pyrrolo[2,3-d]pyrimidin-4-amine [1,2,4]triazolo[1,5-a]pyrimidine Ethyl 4-chloropyrimidine-5-carboxylate Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate Ethyl pyrimidine-4-carboxylate Ethyl pyrimidine-5-carboxylate Imidazo[1,2-c]pyrimidine Methyl pyrimidine-2-carboxylate Methyl pyrimidine-4-carboxylate Methyl pyrimidine-5-carboxylate N,n-dimethylpyrimidin-2-amine N-(9-((2r,5s)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)-9h-purin-6-yl)benzamide N-benzyl-9h-purin-6-amine N-cyclopropylpyrimidin-2-amine N-methyl-n-(4-phenylpyrimidin-2-yl)methanesulfonamide N-methylpyrimidin-2-amine N-methylpyrimidin-4-amine N-phenyl-4-(pyridin-3-yl)pyrimidin-2-amine N-phenylpyrimidin-2-amine N-phenylpyrimidin-4-amine N2,n4-diphenylpyrimidine-2,4-diamine Pyrido[2,3-d]pyrimidine Pyrido[3,2-d]pyrimidine Pyrido[3,4-d]pyrimidine Pyrimidin-2-ol Pyrimidin-2-ylmethanamine Pyrimidin-2-ylmethanol Pyrimidin-4-amine Pyrimidin-4-ol Pyrimidin-5-amine Pyrimidin-5-ol Pyrimidin-5-ylboronic acid Pyrimidine-2,4-diamine Pyrimidine-2-carbonitrile Pyrimidine-2-carboxylic acid Pyrimidine-2-thiol Pyrimidine-4,6(1h,5h)-dione Pyrimidine-4-carbonitrile Pyrimidine-4-carboxylic acid Pyrimidine-5-carbaldehyde Pyrimidine-5-carbonitrile Pyrimidine-5-carboxylic acid Tetrahydropyrimidin-2(1h)-one Thiazolo[5,4-d]pyrimidine Thieno[2,3-d]pyrimidine Thieno[3,2-d]pyrimidine

By Key Group+−

Allylpyrimidine Amino-pyrazolopyrimidine Amino-pyrrolopyrimidine Amino-triazolopyrimidine Aminopyrimidine Benzofuranopyrimidine Bipyrimidine Bromo-pyrazolopyrimidine Bromo-pyrrolopyrimidine Bromo-trifluoromethyl-pyrimidine Bromopyrimidine Butylpyrimidine Chloro-pyrazolopyrimidine Chloro-pyrrolopyrimidine Chloro-triazolopyrimidine Chloro-trifluoromethyl-pyrimidine Chloropyrimidine Cyclopropylpyrimidine Diaminopyrimidine Dibromopyrimidine Dichloropyrimidine Difluoropyrimidine Dihydropyrimidine Dihydroxy-pyrimidine Dihydroxypyrimidine Dimethoxypyrimidine Dimethylpyrimidine Dioxaborolan-pyrimidine Diphenylpyrimidine Ethoxypyrimidine Ethylpyrimidine Fluoropyrimidine Furanopyrimidine Hydrazinylpyrimidine Hydroxy-pyrazolopyrimidine Hydroxypyrimidine Imidazolyl-pyrimidine Imidazopyrimidine Iodo-pyrrolopyrimidine Iodopyrimidine Isopropoxypyrimidine Isopropylpyrimidine Mercaptopyrimidine Methoxypyrimidine Methyl-triazolopyrimidine Methylpyrimidine Methyluracil Nitropyrimidine Phenoxypyrimidine Phenylpyrimidine Piperazin-pyrimidin Piperidine-pyrimidine Propylpyrimidine Pyrazolo-pyrimidine Pyrazolopyrimid-one Pyrazolopyrimidine Pyridin-pyrimidin Pyridopyrimidin Pyrimidinamine Pyrimidine-boronic acid Pyrimidine-boronic acid/ester Pyrimidine-boronic-acid Pyrimidine-hydrochloride Pyrimidine-methanol Pyrimidine-morpholine Pyrimidine-nitrile Pyrimidine-pyrazole Pyrimidinecarbonitrile Pyrimidinecarboxylate Pyrimidinecarboxylic Pyrimidinone Pyrimido-indole Pyrrolidine-pyrimidine Pyrrolopyrimidin-one Pyrrolopyrimidine Pyrrolopyrimidine-carboxylate Pyrrolopyrimidine-carboxylic-acid Tetrahydrofuran-pyrimidine Tetrahydropyrimidine Tetraoxatetradecan Thiazo-pyrimidine Thiazolopyrimidine Thiazopyrimidine Thienopyrimidine Triazolopyrimidine Trichloropyrimidine Trifluoromethyl-phenyl-pyrimidin Trifluoromethyl-pyrimidin-amine Trifluoromethyl-pyrimidin-ol Trifluoromethylpyrimidine Vinylpyrimidine

By Parent Nucleus+−

aromatic heterocycles azetidines benzimidazoles imidazoles indazoles indoles indolines morpholines piperazines piperidines pyrazoles Pyridines pyrrolidines tetrahydroisoquinolines thiazoles thiophenols triazoles

By Functional Group+−

acyl chlorides alcohols aldehydes alkenyls alkyls alkynyls amides amidines amines aryls benzyl bromides benzyl chlorides bromides carboxylic acid salts carboxylic acids Chiral building blocks chlorides difluoromethyls esters ethers fluorinated building blocks hydrazides hydrazines iodides ketones nitriles nitroes oximes phenols phosphoruses sulfamides sulfides sulfonates sulfones sulfonic acids thioesters trifluoromethyls

Heterocyclic related+−

pyr

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