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【结 构 式】

【分子编号】51794

【品名】1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride

【CA登记号】930-28-9

【 分 子 式 】C5H9Cl

【 分 子 量 】104.57916

【元素组成】C 57.43% H 8.67% Cl 33.9%
与该中间体有关的原料药合成路线共 10 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9合成路线10

合成路线1

该中间体在本合成路线中的序号：(VI)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with lmalonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)--3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with cyclopentyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51809 2,6-Difluorophenylacetic acid 85068-28-6 C8H6F2O2 详情 详情
(II) 14338 potassium 3-ethoxy-3-oxopropanoate 6148-64-7 C5H7KO4 详情 详情
(III) 51810 ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate C12H12F2O3 详情 详情
(IV) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(V) 51811 6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C11H8F2N2OS 详情 详情
(VI) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with 2-methylmalonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-2-methyl-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with cyclopentyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51809 2,6-Difluorophenylacetic acid 85068-28-6 C8H6F2O2 详情 详情
(II) 51813 potassium 3-ethoxy-2-methyl-3-oxopropanoate C6H9KO4 详情 详情
(III) 51814 ethyl 4-(2,6-difluorophenyl)-2-methyl-3-oxobutanoate C13H14F2O3 详情 详情
(IV) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(V) 51815 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H10F2N2OS 详情 详情
(VI) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线3

该中间体在本合成路线中的序号：(II)

The alkylation of 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with cyclopentyl chloride (II) by means of K2CO3 gives 2-(cyclopentylsulfanyl)-6-(2,6-difluorobenzyl)pyridmidin-4(3H)-one (III), which is then methylated with Me-Cl and LDA in THF/HMPA to yield the target alpha-methylbenzyl pyrimidinone.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51811 6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C11H8F2N2OS 详情 详情
(II) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情
(III) 51829 2-(cyclopentylsulfanyl)-6-(2,6-difluorobenzyl)-4(3H)-pyrimidinone C16H16F2N2OS 详情 详情

合成路线4

该中间体在本合成路线中的序号：(VII)

The methylation of 2-(2,6-difluorophenyl)acetic acid (I) with Me-Cl and LDA in THF/HMPA gives 2-(2,6-difluorophenyl)propionic acid (II), which is condensed with malonic acid monoethyl ester potassium salt (III) to yield 4´(2,6-difluorophenyl)-3-oxopentanoic acid (IV). The cyclization of (IV) with thiourea (V) affords 6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (VI), which is finally alkylated with cyclopentyl chloride (VII) to provide the target pyrimidinone derivative.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51809 2,6-Difluorophenylacetic acid 85068-28-6 C8H6F2O2 详情 详情
(II) 51820 2-(2,6-difluorophenyl)propionic acid C9H8F2O2 详情 详情
(III) 14338 potassium 3-ethoxy-3-oxopropanoate 6148-64-7 C5H7KO4 详情 详情
(IV) 51830 ethyl 4-(2,6-difluorophenyl)-3-oxopentanoate C13H14F2O3 详情 详情
(V) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VI) 51831 6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H10F2N2OS 详情 详情
(VII) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线5

该中间体在本合成路线中的序号：(II)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with cyclopentyl chloride (II) by means of K2CO3 gives 2-(cyclopentylsulfanyl)-6-(2,6-difluorobenzyl)-5-methylpyridmidin-4(3H)-one (III), which is then methylated with Me-Cl and LDA in THF/HMPA to yield the target alpha-methylbenzyl pyrimidinone.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51815 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H10F2N2OS 详情 详情
(II) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情
(III) 51827 2-(cyclopentylsulfanyl)-6-(2,6-difluorobenzyl)-5-methyl-4(3H)-pyrimidinone C17H18F2N2OS 详情 详情

合成路线6

该中间体在本合成路线中的序号：(VII)

The methylation of 2-(2,6-difluorophenyl)acetic acid (I) with Me-Cl and LDA in THF/HMPA gives 2-(2,6-difluorophenyl)propionic acid (II), which is condensed with 2-methylmalonic acid monoethyl ester potassium salt (III) to yield 4´(2,6-difluorophenyl)-2-methyl-3-oxopentanoic acid (IV). The cyclization of (IV) with thiourea (V) affords 6-[1-(2,6-difluorophenyl)ethyl]-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (VI), which is finally alkylated with cyclopentyl chloride (VII) to provide the target pyrimidinone derivative.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51809 2,6-Difluorophenylacetic acid 85068-28-6 C8H6F2O2 详情 详情
(II) 51820 2-(2,6-difluorophenyl)propionic acid C9H8F2O2 详情 详情
(III) 51813 potassium 3-ethoxy-2-methyl-3-oxopropanoate C6H9KO4 详情 详情
(IV) 51821 ethyl 4-(2,6-difluorophenyl)-2-methyl-3-oxopentanoate C14H16F2O3 详情 详情
(V) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VI) 51822 6-[1-(2,6-difluorophenyl)ethyl]-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C13H12F2N2OS 详情 详情
(VII) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线7

该中间体在本合成路线中的序号：(IV)

When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of compound (III) with cyclopentyl chloride (IV) in alkaline medium afforded the required 2-(cyclopentylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine.

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51791 methyl (Z)-3-hydroxy-4-phenyl-2-butenoate C11H12O3 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 51793 6-benzyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C11H10N2OS 详情 详情
(IV) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线8

该中间体在本合成路线中的序号：(IV)

When 2-methyl-4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 5-methyl-3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of compound (III) with sec-butyl chloride (IV) in alkaline medium afforded the required 2-(sec-butylthio)-5-methyl-6-benzyl-3,4-dihydro-4-oxopyrimidine

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51789 methyl (Z)-3-hydroxy-2-methyl-4-phenyl-2-butenoate C12H14O3 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 51800 6-benzyl-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H12N2OS 详情 详情
(IV) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线9

该中间体在本合成路线中的序号：(IV)

When 4-(3-methylphenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-(3-methylbenzyl)-4-oxo-2-thioxopyrimidine (III). Reaction of the compound (III) with ciclopentyl chloride (IV) in alkaline medium afforded the required 2-(ciclopentylthio)-6-(3-methylbenzyl)-3,4-dihydro-4-oxopyrimidine

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51787 methyl (Z)-3-hydroxy-4-(3-methylphenyl)-2-butenoate C12H14O3 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 51801 6-(3-methylbenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H12N2OS 详情 详情
(IV) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情

合成路线10

该中间体在本合成路线中的序号：(IV)

When 2-methyl-4-(3-methylphenyl)-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 5-methyl-3,4-dihydro-6-(3-methylbenzyl)-4-oxo-2-thioxopyrimidine (III). Reaction of compound (III) with cyclopentyl chloride (IV) in alkaline medium afforded the required 2-(cyclopentylthio)-5-methyl-6-(3-methylbenzyl)-3,4-dihydro-4-oxopyrimidine

参考文献 中间体
合成目标
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51785 methyl (Z)-3-hydroxy-2-methyl-4-(3-methylphenyl)-2-butenoate C13H16O3 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 51799 5-methyl-6-(3-methylbenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C13H14N2OS 详情 详情
(IV) 51794 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride 930-28-9 C5H9Cl 详情 详情
Extended Information