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【结 构 式】 
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【分子编号】51811 【品名】6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone 【CA登记号】 |
【 分 子 式 】C11H8F2N2OS 【 分 子 量 】254.2602064 【元素组成】C 51.96% H 3.17% F 14.94% N 11.02% O 6.29% S 12.61% |
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 lmalonic 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 cyclopentyl 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) | 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)-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)pyridmidin-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) | 51811 | 6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C11H8F2N2OS | 详情 | 详情 | |
| (II) | 51794 | 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride | 930-28-9 | C5H9Cl | 详情 | 详情 |
| (III) | 51829 | 2-(cyclopentylsulfanyl)-6-(2,6-difluorobenzyl)-4(3H)-pyrimidinone | C16H16F2N2OS | 详情 | 详情 |
合成路线3
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 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 methyl chloride 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 |
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 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 isopropyl 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) | 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：(V)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 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 isobutyl 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) | 13624 | 1-Chloro-2-methylpropane; Isobutyl chloride | 513-36-0 | 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 lmalonic 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 1-ethylpropyl 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) | 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 lmalonic 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 cyclohexyl 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) | 51795 | chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride | 542-18-7 | C6H11Cl | 详情 | 详情 |