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【结 构 式】

【分子编号】51822

【品名】6-[1-(2,6-difluorophenyl)ethyl]-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

【CA登记号】

【 分 子 式 】C13H12F2N2OS

【 分 子 量 】282.3139664

【元素组成】C 55.31% H 4.28% F 13.46% N 9.92% O 5.67% S 11.36%
与该中间体有关的原料药合成路线共 7 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1

该中间体在本合成路线中的序号：(VI)

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2

该中间体在本合成路线中的序号：(VI)

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 methyl chloride 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

合成路线3

该中间体在本合成路线中的序号：(VI)

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 isopropyl 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) 29984 2-chloropropane 75-29-6 C3H7Cl 详情 详情

合成路线4

该中间体在本合成路线中的序号：(VI)

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 butyl 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) 51818 n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane 109-69-3 C4H9Cl 详情 详情

合成路线5

该中间体在本合成路线中的序号：(VI)

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 isobutyl 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) 13924 2-Butyl-4-chloro-5-(hydroxymethyl)imidazole; (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol 79047-41-9 C8H13ClN2O 详情 详情

合成路线6

该中间体在本合成路线中的序号：(VI)

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 1-methylpropyl 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) 51797 1-methylpropyl chloride; 2-Chlorobutane; 1-Chloro-1-methylpropane; Sec-Butyl Chloride 78-86-4 C4H9Cl 详情 详情

合成路线7

该中间体在本合成路线中的序号：(VI)

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 cyclohexyl 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) 51795 chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride 542-18-7 C6H11Cl 详情 详情
Extended Information