Chemistry Heterocyclic Building Blocks Pyrimidines 2-(Chloromethyl)Pyrimidine

2-(Chloromethyl)Pyrimidine

These compounds have the same murcko framework: 2-(chloromethyl)pyrimidine

Nucleophilic Substitution (SN2): The chlorine atom in the chloromethyl group is a good leaving group, so the compound can undergo nucleophilic substitution reactions. A nucleophile can attack the carbon bearing the chlorine, leading to substitution of the chlorine atom. This reaction is typical for alkyl halides.
Nucleophilic Substitution (SN1): Under certain conditions, 2-(chloromethyl)pyrimidine may also undergo nucleophilic substitution via an SN1 mechanism, where the chlorine leaves first, forming a carbocation intermediate that is then attacked by a nucleophile.
Arylation Reactions: The pyrimidine ring, being aromatic, can undergo various arylation reactions. For example, it might react with aryl halides or aryl lithium compounds in the presence of a metal catalyst.
Cross-Coupling Reactions: The chloromethyl group can participate in cross-coupling reactions, such as Suzuki coupling or Stille coupling, allowing for the introduction of various substituents.
Nucleophilic Aromatic Substitution (SNAr): The pyrimidine ring, being electron-deficient due to the presence of the chloromethyl group, may undergo nucleophilic aromatic substitution reactions.
Reductive Amination: The chloromethyl group can react with a primary or secondary amine in the presence of a reducing agent to form an amine-substituted pyrimidine.
Ring-Opening Reactions: The chloromethyl group can undergo ring-opening reactions with nucleophiles, leading to the formation of open-chain compounds.
Grignard Reactions: The compound may react with Grignard reagents, forming a new carbon-carbon bond.

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

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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

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pyr

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