n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane -Drug Synthesis Database

【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 合成路线2 合成路线3 合成路线4

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.

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)	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.

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.

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.

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

Extended Information