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【结 构 式】 
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【分子编号】38767 【品名】(3,5-dimethylphenyl)[3-(ethoxymethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl]methyl acetate 【CA登记号】 |
【 分 子 式 】C21H28N2O5 【 分 子 量 】388.4638 【元素组成】C 64.93% H 7.27% N 7.21% O 20.59% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(V)Lithiation of 1-(ethoxymethyl)-5-isopropyl-2-thiouracil (I) by means of LDA in cold THF, followed by condensation with 3,5-dimethylbenzaldehyde (II) gave the 6-(alpha-hydroxybenzyl) derivative (III). Oxidative hydrolysis of the thione function of (III) with H2O2 afforded the corresponding uracil (IV). Acetylation of (IV) with Ac2O in pyridine provided acetate ester (V), which was subjected to hydrogenolysis in the presence of Pd/C to furnish the title benzyl derivative.
| 【1】 Walker, R.T.; Baba, M.; De Clerq, E.; Takashima, H.; Inouye, N.; Ubasawa, M.; Miyasaka, T.; Sekiya, K.; Shigeta, S.; Tanaka, H.; Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents. J Med Chem 1995, 38, 15, 2860. |
| 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) | 27026 | 1-(ethoxymethyl)-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C10H16N2O2S | 详情 | 详情 | |
| (II) | 32915 | 3,5-dimethylbenzaldehyde | 5779-95-3 | C9H10O | 详情 | 详情 |
| (III) | 38765 | 6-[(3,5-dimethylphenyl)(hydroxy)methyl]-1-(ethoxymethyl)-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C19H26N2O3S | 详情 | 详情 | |
| (IV) | 38766 | 6-[(3,5-dimethylphenyl)(hydroxy)methyl]-1-(ethoxymethyl)-5-isopropyl-2,4(1H,3H)-pyrimidinedione | C19H26N2O4 | 详情 | 详情 | |
| (V) | 38767 | (3,5-dimethylphenyl)[3-(ethoxymethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl]methyl acetate | C21H28N2O5 | 详情 | 详情 |
Extended Information