methyl (Z)-3-hydroxy-4-(3-methylphenyl)-2-butenoate -Drug Synthesis Database

【结构式】

【分子编号】51787

【品名】methyl (Z)-3-hydroxy-4-(3-methylphenyl)-2-butenoate

【CA登记号】

【分子式】C₁₂H₁₄O₃

【分子量】206.24136

【元素组成】C 69.89% H 6.84% O 23.27%

与该中间体有关的原料药合成路线共 11 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1

该中间体在本合成路线中的序号：(I)

Condensation of 4-(3-methylphenyl)-3-oxobutanoic acid methyl ester (I) with O-methyl isourea (II) led to the formation of 6-(3-methylbenzyl)-3,4-dihydro-2-methoxy-4-oxopyrimidine (III). Subsequent displacement of the methoxy group linked at C-2 of the pyrimidine ring by treatment with cyclohexoxy potassium salt furnished 2-cyclohexoxy-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)	51787	methyl (Z)-3-hydroxy-4-(3-methylphenyl)-2-butenoate		C₁₂H₁₄O₃	详情	详情
(II)	26657	O-methyl isourea; [Amino(imino)methoxy]methane	52328-05-9	C₂H₆N₂O	详情	详情
(III)	51788	2-methoxy-6-(3-methylbenzyl)-4(3H)-pyrimidinone		C₁₃H₁₄N₂O₂	详情	详情
(IV)	51780	sodium cyclohexanolate		C₆H₁₁NaO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Condensation of 4-(3-methylphenyl)-3-oxobutanoic acid methyl ester (I) with O-methyl isourea (II) led to the formation of 6-(3-methylbenzyl)-3,4-dihydro-2-methoxy-4-oxopyrimidine (III). Subsequent displacement of the methoxy group linked at C-2 of the pyrimidine ring by treatment with sec-butoxy potassium salt furnished 2-sec-butoxy-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)	51787	methyl (Z)-3-hydroxy-4-(3-methylphenyl)-2-butenoate		C₁₂H₁₄O₃	详情	详情
(II)	26657	O-methyl isourea; [Amino(imino)methoxy]methane	52328-05-9	C₂H₆N₂O	详情	详情
(III)	51788	2-methoxy-6-(3-methylbenzyl)-4(3H)-pyrimidinone		C₁₃H₁₄N₂O₂	详情	详情
(IV)	51779	sodium 2-butanolate		C₄H₉NaO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

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 methyl chloride (IV) in alkaline medium afforded the required 2-(methylthio)-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)	51798	methyl chloride; Monochloromethane; Artic; Chloromethane	74-87-3	CH₃Cl	详情	详情

合成路线4

该中间体在本合成路线中的序号：(I)

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 isopropyl chloride (IV) in alkaline medium afforded the required 2-(isopropylthio)-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)	29984	2-chloropropane	75-29-6	C₃H₇Cl	详情	详情

合成路线5

该中间体在本合成路线中的序号：(I)

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 isobutyl chloride (IV) in alkaline medium afforded the required 2-(isobutylthio)-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)	13624	1-Chloro-2-methylpropane; Isobutyl chloride	513-36-0	C₄H₉Cl	详情	详情

合成路线6

该中间体在本合成路线中的序号：(I)

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 sec-butyl chloride (IV) in alkaline medium afforded the required 2-(sec-butylthio)-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)	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：(I)

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8

该中间体在本合成路线中的序号：(I)

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 cyclohexyl chloride (IV) in alkaline medium afforded the required 2-(cyclohexylthio)-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)	51795	chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride	542-18-7	C₆H₁₁Cl	详情	详情

合成路线9

该中间体在本合成路线中的序号：(I)

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 allyl chloride (IV) in alkaline medium afforded the required 2-(allylthio)-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)	13235	Allyl chloride; 3-Chloro-1-propene	107-05-1	C₃H₅Cl	详情	详情

合成路线10

该中间体在本合成路线中的序号：(I)

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 1-chloro-but-2-ene (IV) in alkaline medium afforded the required 2-but-2-enylthio)-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)	36218	(E)-1-chloro-2-butene		C₄H₇Cl	详情	详情

合成路线11

该中间体在本合成路线中的序号：(I)

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 1-chloro-3-methyl-but-2-ene (IV) in alkaline medium afforded the required 2-(3-methyl-but-2-enylthio)-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)	51796	Prenyl Chloride; 1-Chloro-3-methyl-2-butene	503-60-6	C₅H₉Cl	详情	详情

Extended Information