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【结 构 式】

【分子编号】51802

【品名】ethyl 2-ethyl-4-(1-naphthyl)-3-oxobutanoate

【CA登记号】

【 分 子 式 】C18H20O3

【 分 子 量 】284.355

【元素组成】C 76.03% H 7.09% O 16.88%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The condensation of 2-(1-naphthyl)acetonitrile (I) with 2-bromobutyric acid ethyl ester (II) by means of K2CO3 gives 2-ethyl-4-(!-naphthyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) by means of NaOMe yielding 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is condensed with methylsulfanylmethyl iodide (VI) to afford the title 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) 18587 2-(1-naphthyl)acetonitrile 132-75-2 C12H9N 详情 详情
(II) 36668 ethyl 2-bromobutanoate 533-68-6 C6H11BrO2 详情 详情
(III) 51802 ethyl 2-ethyl-4-(1-naphthyl)-3-oxobutanoate C18H20O3 详情 详情
(IV) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(V) 51803 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C17H16N2OS 详情 详情
(VI) 51805 iodomethyl methyl sulfide; iodo(methylsulfanyl)methane C2H5IS 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The condensation of 2-(1-naphthyl)acetonitrile (I) with 2-bromobutyric acid ethyl ester (II) by means of K2CO3 gives 2-ethyl-4-(!-naphthyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) by means of NaOMe yielding 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is condensed with ethylsulfanylmethyl iodide (VI) to afford the title 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) 18587 2-(1-naphthyl)acetonitrile 132-75-2 C12H9N 详情 详情
(II) 36668 ethyl 2-bromobutanoate 533-68-6 C6H11BrO2 详情 详情
(III) 51802 ethyl 2-ethyl-4-(1-naphthyl)-3-oxobutanoate C18H20O3 详情 详情
(IV) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(V) 51803 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C17H16N2OS 详情 详情
(VI) 51804 ethyl iodomethyl sulfide; 1-[(iodomethyl)sulfanyl]ethane C3H7IS 详情 详情
Extended Information