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【结 构 式】

【分子编号】51815

【品名】6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

【CA登记号】

【 分 子 式 】C12H10F2N2OS

【 分 子 量 】268.2870864

【元素组成】C 53.72% H 3.76% F 14.16% N 10.44% O 5.96% S 11.95%
与该中间体有关的原料药合成路线共 14 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11合成路线12合成路线13合成路线14

合成路线1

该中间体在本合成路线中的序号：(V)

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2

该中间体在本合成路线中的序号：(I)

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3

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with methyl chloride by means of K2CO3 gives 6-(2,6-difluorobenzyl)-5-methyl-2-(methylsulfanyl)pyridmidin-4(3H)-one (II), 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) 51828 6-(2,6-difluorobenzyl)-5-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinone C13H12F2N2OS 详情 详情

合成路线4

该中间体在本合成路线中的序号：(V)

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 methyl chloride 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

合成路线5

该中间体在本合成路线中的序号：(V)

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

合成路线6

该中间体在本合成路线中的序号：(V)

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

合成路线7

该中间体在本合成路线中的序号：(V)

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 isobutyl 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) 13624 1-Chloro-2-methylpropane; Isobutyl chloride 513-36-0 C4H9Cl 详情 详情

合成路线8

该中间体在本合成路线中的序号：(V)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with 2-methyllmalonic 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 1-ethylpropyl 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) 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9

该中间体在本合成路线中的序号：(V)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with 2-methyllmalonic 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 cyclohexyl 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) 51795 chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride 542-18-7 C6H11Cl 详情 详情

合成路线10

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with isopropyl chloride (II) by means of K2CO3 gives 6-(2,6-difluorobenzyl)-2-(isopropylsulfanyl)-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) 29984 2-chloropropane 75-29-6 C3H7Cl 详情 详情
(III) 51825 6-(2,6-difluorobenzyl)-2-(isopropylsulfanyl)-5-methyl-4(3H)-pyrimidinone C15H16F2N2OS 详情 详情

合成路线11

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with butyl chloride (II) by means of K2CO3 gives 2-(butylsulfanyl)-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) 51818 n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane 109-69-3 C4H9Cl 详情 详情
(III) 51819 2-(butylsulfanyl)-6-(2,6-difluorobenzyl)-5-methyl-4(3H)-pyrimidinone C16H18F2N2OS 详情 详情

合成路线12

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with isobutyl chloride (II) by means of K2CO3 gives 6-(2,6-difluorobenzyl)-2-(isobutylsulfanyl)-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) 13624 1-Chloro-2-methylpropane; Isobutyl chloride 513-36-0 C4H9Cl 详情 详情
(III) 51823 6-(2,6-difluorobenzyl)-2-(isobutylsulfanyl)-5-methyl-4(3H)-pyrimidinone C16H18F2N2OS 详情 详情

合成路线13

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with 1-methylpropyl chloride (II) by means of K2CO3 gives 6-(2,6-difluorobenzyl)-5-methyl-2-(1-methylpropylsulfanyl)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) 51815 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C12H10F2N2OS 详情 详情
(II) 51797 1-methylpropyl chloride; 2-Chlorobutane; 1-Chloro-1-methylpropane; Sec-Butyl Chloride 78-86-4 C4H9Cl 详情 详情
(III) 51824 2-(sec-butylsulfanyl)-6-(2,6-difluorobenzyl)-5-methyl-4(3H)-pyrimidinone C16H18F2N2OS 详情 详情

合成路线14

该中间体在本合成路线中的序号：(I)

The alkylation of 6-(2,6-difluorobenzyl)-5-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (I) with cyclohexyl chloride (II) by means of K2CO3 gives 2-(cyclohexylsulfanyl)-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) 51795 chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride 542-18-7 C6H11Cl 详情 详情
(III) 51826 2-(cyclohexylsulfanyl)-6-(2,6-difluorobenzyl)-5-methyl-4(3H)-pyrimidinone C18H20F2N2OS 详情 详情
Extended Information