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【结 构 式】 
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【分子编号】27035 【品名】6-benzyl-5-isopropyl-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C14H16N2O2 【 分 子 量 】244.29332 【元素组成】C 68.83% H 6.6% N 11.47% O 13.1% |
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：(XIV)The condensation of ethyl 2-bromo-3-methylbutyrate (IX) with phenylacetonitrile (X) by means of activated Zn in THF gives the ethyl 2-isopropyl-3-oxo-4-phenylbutyrate (XI), which is cyclized with thiourea (XII) by means of sodium ethoxide in refluxing ethanol yielding 6-benzyl-5-isopropyl-2-thioracil (XIII). The desulfurization of (XIII) with a refluxing solution of 10% chloroacetic acid in water affords the corresponding uracil (XIV), which is finally alkylated with chloromethyl ethyl ether (II) and BSA in chloroform.
| 【1】 Larsen, D.K.; et al.; Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J Med Chem 1996, 39, 12, 2427. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 13149 | 1-(Chloromethoxy)ethane; Chloromethyl ethyl ether | 3188-13-4 | C3H7ClO | 详情 | 详情 |
| (IX) | 27032 | 2-Bromoisovalerianic acid ethyl ester; ethyl 2-bromo-3-methylbutanoate | 609-12-1 | C7H13BrO2 | 详情 | 详情 |
| (X) | 17046 | Phenylacetonitrile; 2-phenylacetonitrile; Benzyl cyanide | 140-29-4 | C8H7N | 详情 | 详情 |
| (XI) | 27033 | ethyl 2-isopropyl-3-oxo-4-phenylbutanoate | C15H20O3 | 详情 | 详情 | |
| (XII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (XIII) | 27034 | 6-benzyl-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C14H16N2OS | 详情 | 详情 | |
| (XIV) | 27035 | 6-benzyl-5-isopropyl-2,4(1H,3H)-pyrimidinedione | C14H16N2O2 | 详情 | 详情 |
Extended Information