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【结 构 式】

【分子编号】51818

【品名】n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane

【CA登记号】109-69-3

【 分 子 式 】C4H9Cl

【 分 子 量 】92.56816

【元素组成】C 51.9% H 9.8% Cl 38.3%

与该中间体有关的原料药合成路线共 4 条

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 malonic 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 butyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

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) 51818 n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane 109-69-3 C4H9Cl 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 butyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

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3

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 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.

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 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.

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
Extended Information