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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
2-Fluoro-3-bromo-4-(oxan-4-yl)pyridine 2-Fluoro-3-bromo-4-(oxan-4-yl)pyridine 1622843-14-4 C10H11BrFNO
2-Fluoro-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2-Fluoro-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2223036-95-9 C17H19BFNO3
2-Fluoro-6-(2-fluorophenyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(2-fluorophenyl)pyridine-3-boronic acid pinacol ester 2223037-30-5 C17H18BF2NO2
2-Fluoro-6-(pyrimidin-5-yl)pyridine 2-Fluoro-6-(pyrimidin-5-yl)pyridine 1563529-89-4 C9H6FN3
2-Fluoro-6-(thiazol-2-yl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(thiazol-2-yl)pyridine-3-boronic acid pinacol ester 2223049-01-0 C14H16BFN2O2S
2-Fluoro-6-phenylpyridine-3-boronic acid pinacol ester 2-Fluoro-6-phenylpyridine-3-boronic acid pinacol ester 2223036-20-0 C17H19BFNO2
2-Hydroxy-3-(3-thienyl)pyridine 2-Hydroxy-3-(3-thienyl)pyridine 1027262-47-0 C9H7NOS
2-Hydroxy-3-(4-trifluoromethylphenyl)pyridine 2-Hydroxy-3-(4-trifluoromethylphenyl)pyridine 426823-47-4 C12H8F3NO
2-hydroxy-4-(1H-3-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(1H-3-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412959-81-9 C12H16N4O
2-Hydroxy-4-(1H-4-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(1H-4-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 1412961-24-0 C11H14N4O
2-Hydroxy-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 1412959-92-2 C11H13N3O
2-hydroxy-4-(2-chlorophenyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(2-chlorophenyl)-6-(tert-butyl)pyrimidine 1412953-00-4 C14H15ClN2O
2-hydroxy-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1412955-51-1 C14H23N3O
2-hydroxy-4-(2-thienyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(2-thienyl)-6-cyclopropylpyrimidine 1412960-54-3 C11H10N2OS
2-Hydroxy-4-(3-chlorophenyl)-6-methylpyrimidine 2-Hydroxy-4-(3-chlorophenyl)-6-methylpyrimidine 1412959-38-6 C11H9ClN2O
2-Hydroxy-4-(3-furyl)-6-methylpyrimidine 2-Hydroxy-4-(3-furyl)-6-methylpyrimidine 1412956-91-2 C9H8N2O2
2-Hydroxy-4-(4-chlorophenyl)-6-methylpyrimidine 2-Hydroxy-4-(4-chlorophenyl)-6-methylpyrimidine 19927-53-8 C11H9ClN2O
2-Hydroxy-4-(4-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(4-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 1412955-37-3 C13H21N3O
2-hydroxy-4-(4-tetrahydropyranyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(4-tetrahydropyranyl)-6-cyclopropylpyrimidine 1412960-18-9 C12H16N2O2
2-Hydroxy-4-(iso-propoxy)-6-methylpyrimidine 2-Hydroxy-4-(iso-propoxy)-6-methylpyrimidine 25589-24-6 C8H12N2O2
2-hydroxy-4-(n-propyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(n-propyl)-6-cyclopropylpyrimidine 1412956-39-8 C10H14N2O
2-hydroxy-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 1412956-63-8 C13H15N3O
2-Hydroxy-4-(pyrimidin-5-yl)-6-methylpyrimidine 2-Hydroxy-4-(pyrimidin-5-yl)-6-methylpyrimidine 1412958-32-7 C9H8N4O
2-hydroxy-4-cyclohexyl-6-cyclopropylpyrimidine 2-hydroxy-4-cyclohexyl-6-cyclopropylpyrimidine 1622840-85-0 C13H18N2O
2-hydroxy-4-ethyl-6-(tert-butyl)pyrimidine 2-hydroxy-4-ethyl-6-(tert-butyl)pyrimidine 1412955-36-2 C10H16N2O
2-Iodo-6-cyanopyridine-4-boronic acid pinacol ester 2-Iodo-6-cyanopyridine-4-boronic acid pinacol ester 2223048-26-6 C12H14BIN2O2
2-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2223044-11-7 C13H22BNO2S
2-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2223028-90-6 C15H21BF3NO2
2-isopropyl-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-isopropyl-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223041-58-3 C19H30BNO3
2-methyl-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)thiazole 2-methyl-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)thiazole 1402173-93-6 C15H19BN2O2S
2-Methyl-5-(iso-butyl)pyridine-3-boronic acid pinacol ester 2-Methyl-5-(iso-butyl)pyridine-3-boronic acid pinacol ester 2223051-39-4 C16H26BNO2
2-Methyl-5-(sec-butyl)pyridine-3-boronic acid pinacol ester 2-Methyl-5-(sec-butyl)pyridine-3-boronic acid pinacol ester 2223006-99-1 C16H26BNO2
2-Methyl-6-(cyclopropyl)pyridine-3-boronic acid pinacol ester 2-Methyl-6-(cyclopropyl)pyridine-3-boronic acid pinacol ester 1951411-47-4 C15H22BNO2
2-propoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-propoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 1352037-23-0 C12H20BNO3S
2-Trifluoromethyl-6-(tert-butoxy)pyridine-4-boronic acid pinacol ester 2-Trifluoromethyl-6-(tert-butoxy)pyridine-4-boronic acid pinacol ester 2223011-94-5 C16H23BF3NO3
3-(2-Tolyl)pyridine-2-boronic acid pinacol ester 3-(2-Tolyl)pyridine-2-boronic acid pinacol ester 2223035-18-3 C18H22BNO2
3-(3-Trifluoromethylphenyl)pyridine-2-boronic acid pinacol ester 3-(3-Trifluoromethylphenyl)pyridine-2-boronic acid pinacol ester 2223012-26-6 C18H19BF3NO2
3-(4-Tolyl)pyridine-2-boronic acid pinacol ester 3-(4-Tolyl)pyridine-2-boronic acid pinacol ester 2223053-31-2 C18H22BNO2
3-(5-Bromopyridin-2-yl)phenylboronic acid pinacol ester 3-(5-Bromopyridin-2-yl)phenylboronic acid pinacol ester 2223048-70-0 C17H19BBrNO2
3-(Cyclopentoxy)pyridine-2-boronic acid pinacol ester 3-(Cyclopentoxy)pyridine-2-boronic acid pinacol ester 2223042-48-4 C16H24BNO3
3-(Ethoxy)pyridine-2-boronic acid pinacol ester 3-(Ethoxy)pyridine-2-boronic acid pinacol ester 2223013-08-7 C13H20BNO3
3-(ethyl-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(ethyl-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-25-0 C13H20BNO2
3-(propoxy-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(propoxy-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-21-6 C14H22BNO3
3-(Pyridin-4-yl)pyridine-2-boronic acid pinacol ester 3-(Pyridin-4-yl)pyridine-2-boronic acid pinacol ester 2223013-02-1 C16H19BN2O2
3-(tert-Butyl)pyridine-4-boronic acid pinacol ester 3-(tert-Butyl)pyridine-4-boronic acid pinacol ester 2223037-89-4 C15H24BNO2
3-Amino-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 3-Amino-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 1215073-71-4 C11H11N5
3-Amino-6-(5-fluoropyridyl-2-yl)pyridazine 3-Amino-6-(5-fluoropyridyl-2-yl)pyridazine 1215073-65-6 C9H7FN4
3-Amino-6-(cyclohexyl)pyridazine 3-Amino-6-(cyclohexyl)pyridazine 105538-00-9 C10H15N3
3-Amino-6-(tert-butyl)pyridine-4-boronic acid pinacol ester 3-Amino-6-(tert-butyl)pyridine-4-boronic acid pinacol ester 2223036-32-4 C15H25BN2O2
3-Bromo-1-(cyclohexyl)-1H-pyrrole 3-Bromo-1-(cyclohexyl)-1H-pyrrole 1622843-92-8 C10H14BrN
3-Bromo-2-amino-5-(pyrrolidino)pyridine 3-Bromo-2-amino-5-(pyrrolidino)pyridine 1381936-23-7 C9H12BrN3
3-Bromo-2-fluoro-6-(oxan-4-yl)pyridine 3-Bromo-2-fluoro-6-(oxan-4-yl)pyridine 1622843-18-8 C10H11BrFNO
3-Bromo-2-fluoro-6-cyclopentylpyridine 3-Bromo-2-fluoro-6-cyclopentylpyridine 1622838-85-0 C10H11BrFN
3-Bromo-4-chloro-6-(iso-propyl)pyridine 3-Bromo-4-chloro-6-(iso-propyl)pyridine 1353856-13-9 C8H9BrClN
3-Bromo-5-(1H-pyridin-2-one)phenylboronic acid pinacol ester 3-Bromo-5-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2223030-99-5 C17H19BBrNO3
3-Bromo-6-(2-fluorophenyl)pyridazine 3-Bromo-6-(2-fluorophenyl)pyridazine 1036226-83-1 C10H6BrFN2
3-Bromo-6-(3-methoxyphenyl)pyridazine 3-Bromo-6-(3-methoxyphenyl)pyridazine 1215071-29-6 C11H9BrN2O
3-Bromo-6-(3-trifluoromethylphenyl)pyridazine 3-Bromo-6-(3-trifluoromethylphenyl)pyridazine 1215072-28-8 C11H6BrF3N2
3-Bromo-6-(cyclopentoxy)pyridazine 3-Bromo-6-(cyclopentoxy)pyridazine 1027513-37-6 C9H11BrN2O
3-Bromo-6-(iso-propenyl)pyridazine 3-Bromo-6-(iso-propenyl)pyridazine 1314354-56-7 C7H7BrN2
3-Phenylpyridine-2-boronic acid pinacol ester 3-Phenylpyridine-2-boronic acid pinacol ester 2223012-78-8 C17H20BNO2
4-(2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223047-80-9 C19H28BNO3
4-(2-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 4-(2-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 1417517-83-9 C10H7F3N4
4-(3-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(3-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223044-00-4 C19H28BNO3
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)thiazole 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)thiazole 2223035-99-0 C14H17BN2O2S
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiazole 2223036-47-1 C12H15BN2O2S2
4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2'-bipyridin]-2-one 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2'-bipyridin]-2-one 1402172-62-6 C16H19BN2O3
4-(4-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(4-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223042-24-6 C19H28BNO3
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine-2,2,3,3,5,5,6,6-d8 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine-2,2,3,3,5,5,6,6-d8 2241875-47-6 C15H23BN2O3
4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine-2,2,3,3,5,5,6,6-d8 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine-2,2,3,3,5,5,6,6-d8 2241870-12-0 C15H23BN2O3
4-(Cyclohexyl)-1,3,5-triazin-2-amine 4-(Cyclohexyl)-1,3,5-triazin-2-amine 1340492-50-3 C9H14N4
4-(iso-Butyl)-1,3,5-triazin-2-amine 4-(iso-Butyl)-1,3,5-triazin-2-amine 1340279-45-9 C7H12N4
4-(iso-Propyl)-1,3,5-triazin-2-amine 4-(iso-Propyl)-1,3,5-triazin-2-amine 1417517-76-0 C6H10N4
4-(methoxy-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(methoxy-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241874-87-1 C12H18BNO3
4-(N-Boc-morpholin-2-yl)pyrimidine 4-(N-Boc-morpholin-2-yl)pyrimidine 1622835-33-9 C13H19N3O3
4-(n-Propyl)pyridine-3-boronic acid pinacol ester 4-(n-Propyl)pyridine-3-boronic acid pinacol ester 2223051-43-0 C14H22BNO2
4-(propoxy-d7)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(propoxy-d7)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241874-88-2 C14H22BNO3
4,5-Dibromo-2-(tetrahydrofuran-3-yl)pyridine 4,5-Dibromo-2-(tetrahydrofuran-3-yl)pyridine 1381938-14-2 C9H9Br2NO
4-Amino-2-(iso-propyl)-6-(1H-pyridin-2-one)-pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-pyridin-2-one)-pyrimidine 1412955-30-6 C12H14N4O
4-Amino-2-(iso-propyl)-6-(2-thienyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(2-thienyl)pyrimidine 1248611-47-3 C11H13N3S
4-Amino-2-(iso-propyl)-6-morpholinopyrimidine 4-Amino-2-(iso-propyl)-6-morpholinopyrimidine 1412958-26-9 C11H18N4O
4-Amino-2-(pyridin-3-yl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(pyridin-3-yl)pyrimidine-5-boronic acid pinacol ester 2223053-32-3 C15H19BN4O2
4-Amino-2-cyclopropyl-6-(3-methylpiperidin-1-yl)pyrimidine 4-Amino-2-cyclopropyl-6-(3-methylpiperidin-1-yl)pyrimidine 1412959-84-2 C13H20N4
4-Amino-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-Amino-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 1412955-90-8 C13H20N4
4-Amino-2-phenylpyrimidine-5-boronic acid pinacol ester 4-Amino-2-phenylpyrimidine-5-boronic acid pinacol ester 2223050-34-6 C16H20BN3O2
4-amino-6-(3-furyl)-2-methylpyrimidine 4-amino-6-(3-furyl)-2-methylpyrimidine 1412959-77-3 C9H9N3O
4-amino-6-cyclohexyl-2-methylpyrimidine 4-amino-6-cyclohexyl-2-methylpyrimidine 1412955-06-6 C11H17N3
4-Bromo-2-(1H-Pyrrol-1-yl)thiazole 4-Bromo-2-(1H-Pyrrol-1-yl)thiazole 1086381-65-8 C7H5BrN2S
4-Bromo-2-(2-methoxyphenyl)pyrimidine 4-Bromo-2-(2-methoxyphenyl)pyrimidine 1142195-82-1 C11H9BrN2O
4-Bromo-2-(cyclobutoxy)pyrimidine 4-Bromo-2-(cyclobutoxy)pyrimidine 1159820-38-8 C8H9BrN2O
4-Bromo-2-(iso-propyl)-6-(2-thienyl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(2-thienyl)pyrimidine 1412958-14-5 C11H11BrN2S
4-Bromo-2-(iso-propyl)-6-(3-thienyl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(3-thienyl)pyrimidine 1412955-65-7 C11H11BrN2S
4-Bromo-2-(N,N-methylethylamino)pyrimidine 4-Bromo-2-(N,N-methylethylamino)pyrimidine 959240-60-9 C7H10BrN3
4-Bromo-2-(oxolan-3-yl)-5-fluoropyridine 4-Bromo-2-(oxolan-3-yl)-5-fluoropyridine 1643575-97-6 C9H9BrFNO
4-Bromo-2-amino-5-(2-pyridyl)pyridine 4-Bromo-2-amino-5-(2-pyridyl)pyridine 1381938-19-7 C10H8BrN3
4-Bromo-2-amino-5-(4-pyridyl)pyridine 4-Bromo-2-amino-5-(4-pyridyl)pyridine 1381938-18-6 C10H8BrN3
4-Bromo-2-cyclopropyl-6-(2-fluorophenyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-fluorophenyl)pyrimidine 1412958-38-3 C13H10BrFN2
4-Bromo-2-cyclopropyl-6-(2-thienyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-thienyl)pyrimidine 1412961-98-8 C11H9BrN2S
4-Bromo-2-cyclopropyl-6-(5-pyrimidyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(5-pyrimidyl)pyrimidine 1412960-75-8 C11H9BrN4
4-bromo-2-cyclopropyl-6-(n-propyl)pyrimidine 4-bromo-2-cyclopropyl-6-(n-propyl)pyrimidine 1412958-67-8 C10H13BrN2
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