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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
4-bromo-2-propyl-6-(trifluoromethyl)pyridine 4-bromo-2-propyl-6-(trifluoromethyl)pyridine 2460492-95-7 C9H9BrF3N
4-bromo-2-(difluoromethyl)-6-isopropylpyridine 4-bromo-2-(difluoromethyl)-6-isopropylpyridine 2460501-28-2 C9H10BrF2N
2-bromo-4-(1H-imidazol-2-yl)pyrimidine 2-bromo-4-(1H-imidazol-2-yl)pyrimidine 2256748-28-2 C7H5BrN4
2-cyclopentyl-6-methylpyridin-4-amine 2-cyclopentyl-6-methylpyridin-4-amine 1368101-02-3 C11H16N2
6-bromo-5-(sec-butyl)pyridin-3-amine 6-bromo-5-(sec-butyl)pyridin-3-amine 2460493-74-5 C9H13BrN2
3-bromo-5-ethylpyridin-4-ol 3-bromo-5-ethylpyridin-4-ol 2460500-47-2 C7H8BrNO
5-bromo-4-chloro-2-propylpyrimidine 5-bromo-4-chloro-2-propylpyrimidine 1532505-16-0 C7H8BrClN2
2-(4-bromo-2-fluoro-1H-imidazol-1-yl)pyrimidine 2-(4-bromo-2-fluoro-1H-imidazol-1-yl)pyrimidine 2460494-48-6 C7H4BrFN4
3-bromo-4-(sec-butyl)-4H-1,2,4-triazole 3-bromo-4-(sec-butyl)-4H-1,2,4-triazole 2460492-31-1 C6H10BrN3
5-(3-bromo-4H-1,2,4-triazol-4-yl)pyrimidine 5-(3-bromo-4H-1,2,4-triazol-4-yl)pyrimidine 2460492-07-1 C6H4BrN5
5-(3-bromo-4H-1,2,4-triazol-4-yl)thiazole 5-(3-bromo-4H-1,2,4-triazol-4-yl)thiazole 2460490-09-7 C5H3BrN4S
3-bromo-4-(p-tolyl)-4H-1,2,4-triazole 3-bromo-4-(p-tolyl)-4H-1,2,4-triazole 2460492-46-8 C9H8BrN3
4-(m-tolyl)-4H-1,2,4-triazol-3-amine 4-(m-tolyl)-4H-1,2,4-triazol-3-amine 1547873-62-0
4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine 4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine 2460494-47-5 C9H7F3N4
4-cyclopentyl-4H-1,2,4-triazol-3-amine 4-cyclopentyl-4H-1,2,4-triazol-3-amine 1250640-49-3 C7H12N4
4-(sec-butyl)-5-methyl-4H-1,2,4-triazol-3-amine 4-(sec-butyl)-5-methyl-4H-1,2,4-triazol-3-amine 2460491-81-8 C7H14N4
3,5-dibromo-4-isopropyl-4H-1,2,4-triazole 3,5-dibromo-4-isopropyl-4H-1,2,4-triazole 2460490-16-6 C5H7Br2N3
3,5-dibromo-4-cyclopentyl-4H-1,2,4-triazole 3,5-dibromo-4-cyclopentyl-4H-1,2,4-triazole 2460491-97-6 C7H9Br2N3
3-bromo-5-(thiophen-3-yl)-4H-1,2,4-triazole 3-bromo-5-(thiophen-3-yl)-4H-1,2,4-triazole 2460491-95-4 C6H4BrN3S
5-bromo-4-(2-methoxyphenyl)-1H-1,2,3-triazole 5-bromo-4-(2-methoxyphenyl)-1H-1,2,3-triazole 2460492-28-6 C9H8BrN3O
4-(tetrahydrofuran-2-yl)-1H-1,2,3-triazole 4-(tetrahydrofuran-2-yl)-1H-1,2,3-triazole 2460490-20-2 C6H9N3O
4-bromo-1-cyclopropyl-5-isopropyl-1H-1,2,3-triazole 4-bromo-1-cyclopropyl-5-isopropyl-1H-1,2,3-triazole 2460501-41-9 C8H12BrN3
3-cyclopentyl-5-methyl-4H-1,2,4-triazole 3-cyclopentyl-5-methyl-4H-1,2,4-triazole 1094563-78-6 C8H13N3
4-(5-bromopyridin-3-yl)pyrimidine 4-(5-bromopyridin-3-yl)pyrimidine 1211579-53-1 C9H6BrN3
2-(tetrahydrofuran-2-yl)thiazol-5-amine 2-(tetrahydrofuran-2-yl)thiazol-5-amine 2460492-66-2 C7H10N2OS
3-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridazine 3-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridazine 2460500-71-2 C8H7BrN4
3-bromo-4-cyclopropylpyridin-2-amine 3-bromo-4-cyclopropylpyridin-2-amine 1824631-53-9 C8H9BrN2
3-bromo-2-fluoro-6-(thiophen-2-yl)pyridine 3-bromo-2-fluoro-6-(thiophen-2-yl)pyridine 2600399-87-7 C9H5BrFNS
3-bromo-6-(3-bromophenyl)-2-fluoropyridine 3-bromo-6-(3-bromophenyl)-2-fluoropyridine 2600400-02-8 C11H6Br2FN
3-bromo-2-methyl-6-(oxetan-3-yl)pyridine 3-bromo-2-methyl-6-(oxetan-3-yl)pyridine 2600400-35-7 C9H10BrNO
4-bromo-2-(oxetan-3-yl)-6-(trifluoromethyl)pyridine 4-bromo-2-(oxetan-3-yl)-6-(trifluoromethyl)pyridine 2645418-83-1 C9H7BrF3NO
1-(m-tolyl)-1H-1,2,3-triazol-4-amine 1-(m-tolyl)-1H-1,2,3-triazol-4-amine 1462364-25-5 C9H10N4
4-bromo-1-(2-fluorophenyl)-1H-1,2,3-triazole 4-bromo-1-(2-fluorophenyl)-1H-1,2,3-triazole 2256748-68-0 C8H5BrFN3
4-chloro-2-isopropyl-5-(trifluoromethyl)pyrimidine 4-chloro-2-isopropyl-5-(trifluoromethyl)pyrimidine 2645419-24-3 C8H8ClF3N2
2,3,5-trimethylpyridin-4-amine 2,3,5-trimethylpyridin-4-amine 1186329-61-2 C8H12N2
2-bromo-4-((tetrahydrofuran-2-yl)methoxy)pyridine 2-bromo-4-((tetrahydrofuran-2-yl)methoxy)pyridine 2645411-75-0 C10H12BrNO2
2-bromo-5-((tetrahydro-2H-pyran-2-yl)methoxy)pyridine 2-bromo-5-((tetrahydro-2H-pyran-2-yl)methoxy)pyridine 1701701-17-8 C11H14BrNO2
2-((2,4-dimethoxybenzyl)oxy)-4-fluoropyridine 2-((2,4-dimethoxybenzyl)oxy)-4-fluoropyridine 2256748-01-1 C14H14FNO3
2-bromo-4-(tert-butoxy)-6-fluoropyridine 2-bromo-4-(tert-butoxy)-6-fluoropyridine 2645419-86-7 C9H11BrFNO
2,2'-dibromo-5,5'-bipyrimidine 2,2'-dibromo-5,5'-bipyrimidine 2186709-26-0 C8H4Br2N4
3-bromo-5-(3-methylbicyclo[1.1.1]pentan-1-yl)pyridine 3-bromo-5-(3-methylbicyclo[1.1.1]pentan-1-yl)pyridine 2697157-06-3 C11H12BrN
3-(4-bromo-1H-1,2,3-triazol-1-yl)pyridazine 3-(4-bromo-1H-1,2,3-triazol-1-yl)pyridazine 2256754-42-2 C6H4BrN5
5-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)thiazole 5-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)thiazole 2697162-30-2 C9H10BrNS
5-bromo-2-(pyridin-3-yl)oxazole 5-bromo-2-(pyridin-3-yl)oxazole 1391737-86-2 C8H5BrN2O
1-(2-fluoropyridin-4-yl)-1H-1,2,3-triazol-4-amine 1-(2-fluoropyridin-4-yl)-1H-1,2,3-triazol-4-amine 2256754-52-4 C7H6FN5
5-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methoxypyridine 5-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methoxypyridine 2256754-59-1 C8H7BrN4O
4-(pyrrolidin-3-yl)-2-(trifluoromethyl)pyridine 4-(pyrrolidin-3-yl)-2-(trifluoromethyl)pyridine 2697156-04-8 C10H11F3N2
5-bromo-1-propyl-1H-1,2,3-triazole 5-bromo-1-propyl-1H-1,2,3-triazole 1890489-46-9 C5H8BrN3
5-bromo-8-ethylquinoxaline 5-bromo-8-ethylquinoxaline 2806729-53-1 C10H9BrN2
2-(3-cyclopropylphenyl)morpholine 2-(3-cyclopropylphenyl)morpholine 1521574-10-6
2-(6-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 2-(6-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 2355513-62-9 C10H10BrNO2
2-(2-aminopyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2-(2-aminopyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2806728-89-0 C9H11N3O2
2-(5-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2-(5-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806719-23-1 C9H10N2O3
2-(4-aminopyridin-2-yl)tetrahydro-4H-pyran-4-one 2-(4-aminopyridin-2-yl)tetrahydro-4H-pyran-4-one 2806719-29-7 C10H12N2O2
3-(5-aminopyridin-2-yl)tetrahydro-4H-pyran-4-one 3-(5-aminopyridin-2-yl)tetrahydro-4H-pyran-4-one 2806728-45-8 C10H12N2O2
3-(4-aminopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 3-(4-aminopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806729-71-3 C9H11N3O2
3-(2-bromopyrimidin-4-yl)tetrahydro-4H-pyran-4-one 3-(2-bromopyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2806721-17-3 C9H9BrN2O2
5-bromo-2-ethyl-3-fluoropyridine 5-bromo-2-ethyl-3-fluoropyridine 1346539-79-4 C7H7BrFN
tert-butyl 4-(4-aminopyrimidin-2-yl)piperidine-1-carboxylate tert-butyl 4-(4-aminopyrimidin-2-yl)piperidine-1-carboxylate 1440427-75-7 C14H22N4O2
2-chloro-4-methylpyrido[2,3-d]pyrimidine 2-chloro-4-methylpyrido[2,3-d]pyrimidine 2891520-39-9 C8H6ClN3
3-bromo-6-cyclohexyl-2-(trifluoromethyl)pyridine 3-bromo-6-cyclohexyl-2-(trifluoromethyl)pyridine 2891510-69-1 C12H13BrF3N
tert-butyl 4-(5-bromo-6-(trifluoromethyl)pyridin-2-yl)piperidine-1-carboxylate tert-butyl 4-(5-bromo-6-(trifluoromethyl)pyridin-2-yl)piperidine-1-carboxylate 2891512-23-3 C16H20BrF3N2O2
6-bromo-3-(tetrahydro-2H-pyran-4-yl)-2-(trifluoromethyl)pyridine 6-bromo-3-(tetrahydro-2H-pyran-4-yl)-2-(trifluoromethyl)pyridine 2891511-29-6 C11H11BrF3NO
5-bromo-2-(tetrahydrofuran-2-yl)pyridin-4-ol 5-bromo-2-(tetrahydrofuran-2-yl)pyridin-4-ol 2891518-99-1 C9H10BrNO2
5-bromo-2-(tetrahydrofuran-2-yl)pyridin-4-amine 5-bromo-2-(tetrahydrofuran-2-yl)pyridin-4-amine 2723941-02-2 C9H11BrN2O
5-bromo-2,4-dicyclopropylthiazole 5-bromo-2,4-dicyclopropylthiazole 1823425-00-8 C9H10BrNS
tert-butyl 5-bromo-2,3-dihydro-4H-1,4-oxazine-4-carboxylate tert-butyl 5-bromo-2,3-dihydro-4H-1,4-oxazine-4-carboxylate 2891512-18-6 C9H14BrNO3
tert-butyl 3-(4-aminopyridin-2-yl)morpholine-4-carboxylate tert-butyl 3-(4-aminopyridin-2-yl)morpholine-4-carboxylate 2360097-03-4 C14H21N3O3
tert-butyl 3-(2-chloropyrimidin-4-yl)morpholine-4-carboxylate tert-butyl 3-(2-chloropyrimidin-4-yl)morpholine-4-carboxylate 2891511-98-9 C13H18ClN3O3
tert-butyl 3-methyl-3,4-dihydropyridine-1(2H)-carboxylate tert-butyl 3-methyl-3,4-dihydropyridine-1(2H)-carboxylate 2613352-58-0 C11H19NO2
2-methyl-5-(trifluoromethyl)pyrimidin-4-ol 2-methyl-5-(trifluoromethyl)pyrimidin-4-ol 2891519-01-8 C6H5F3N2O
5-bromo-2-chloro-3-cyclopropyl-4-fluoropyridine 5-bromo-2-chloro-3-cyclopropyl-4-fluoropyridine 2952896-34-1 C8H6BrClFN
tert-butyl 2-(2-methylpyridin-4-yl)morpholine-4-carboxylate tert-butyl 2-(2-methylpyridin-4-yl)morpholine-4-carboxylate 2952896-36-3 C15H22N2O3
2-chloro-4-(((2-fluoropyridin-4-yl)oxy)methyl)pyrimidine 2-chloro-4-(((2-fluoropyridin-4-yl)oxy)methyl)pyrimidine 2973762-65-9 C10H7ClFN3O
4-fluoro-3-iodopyridin-2-ol 4-fluoro-3-iodopyridin-2-ol 1806576-99-7 C5H3FINO
3-bromo-4-cyclopropyl-2-(trifluoromethyl)pyridine 3-bromo-4-cyclopropyl-2-(trifluoromethyl)pyridine 2294947-12-7 C9H7BrF3N
6-methoxy-5-(tetrahydrofuran-3-yl)pyridin-3-amine 6-methoxy-5-(tetrahydrofuran-3-yl)pyridin-3-amine 2294949-91-8 C10H14N2O2
5-bromo-2-cyclopentyl-3-methoxypyridine 5-bromo-2-cyclopentyl-3-methoxypyridine 2294947-89-8 C11H14BrNO
3-(2,4-dibromo-1H-imidazol-1-yl)pyridine 3-(2,4-dibromo-1H-imidazol-1-yl)pyridine 2294950-34-6 C8H5Br2N3
2-(2,5-dibromo-1H-imidazol-1-yl)pyridine 2-(2,5-dibromo-1H-imidazol-1-yl)pyridine 2294957-72-3 C8H5Br2N3
5-bromo-1-(pyridin-3-yl)-1H-imidazol-2-amine 5-bromo-1-(pyridin-3-yl)-1H-imidazol-2-amine 2294956-93-5 C8H7BrN4
4-fluoro-6-methoxy-5-methylpyridin-3-amine 4-fluoro-6-methoxy-5-methylpyridin-3-amine 2294943-88-5 C7H9FN2O
5-bromo-1-cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 5-bromo-1-cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2364586-03-6 C13H21BBrN3O2
5-fluoro-1-(tetrahydrofuran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 5-fluoro-1-(tetrahydrofuran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2364572-89-2 C12H19BFN3O3
2-(oxetan-3-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(oxetan-3-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2364585-56-6 C14H20BNO4
2-(2-isopropylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(2-isopropylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2364585-93-1 C13H21BO2S
1-cyclopropyl-5-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 1-cyclopropyl-5-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2460672-68-6 C14H24BN3O2
4-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyrimidine 4-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyrimidine 2460672-41-5 C14H19BN4O2
(2-methyl-6-(thiazol-4-yl)pyridin-3-yl)boronic acid (2-methyl-6-(thiazol-4-yl)pyridin-3-yl)boronic acid 2710290-32-5 C9H9BN2O2S
tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-yl)carbamate tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-yl)carbamate
5-(2,2-difluorocyclopropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(2,2-difluorocyclopropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710293-41-5 C14H18BF2NO2
4,6-difluoro-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 4,6-difluoro-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 2710293-65-3 C13H19BF2N2O2
2,4-difluoro-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2,4-difluoro-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710293-80-2 C16H22BF2NO3
4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol 2710293-86-8 C11H15BClNO3
2-(azetidin-1-yl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(azetidin-1-yl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710294-02-1 C14H20BFN2O2
5-(2-methoxyethoxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(2-methoxyethoxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710294-18-9 C14H22BNO4
7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine 7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine 2710294-40-7 C12H15BClN3O2
2,4-difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2,4-difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710294-46-3 C11H14BF2NO2
5-(bicyclo[1.1.1]pentan-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(bicyclo[1.1.1]pentan-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2710295-75-1 C16H22BNO2
2-(3-methylbicyclo[1.1.1]pentan-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-(3-methylbicyclo[1.1.1]pentan-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2710295-81-9 C16H23BN2O2
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