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【结 构 式】 
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【分子编号】10785 【品名】2-[[2-(acetamido)-6-chloro-9H-purin-9-yl]methoxy]ethyl acetate 【CA登记号】 |
【 分 子 式 】C12H14ClN5O4 【 分 子 量 】327.72716 【元素组成】C 43.98% H 4.31% Cl 10.82% N 21.37% O 19.53% |
合成路线1
该中间体在本合成路线中的序号：(II)A new synthesis of A-515-U has been reported. The compound can be synthesized in two similar ways: 1) The reaction of 9-(2-acetoxyethoxymethyl)-2-(acetylamino)-6,9-dihydro-1H-purin-6-one (I) with POCl3 and 2,4,6-trimethylpyridine in refluxing acetonitrile gives 9-(2-acetoxyethoxymethyl)-2-(acetylamino)-6-chloro-9H-purine (II), which is dechlorinated with formic acid - triethylamine and Pd/C in refluxing acetone, yielding 9-(2-acetoxyethoxymethyl)-2-(acetylamino)-9H-purine (III). Finally, this compound is deacetylated in water. 2) Purine (I) is partially deacetylated with triethylamine in refluxing ethanol to give 9-(2-acetoxyethoxymethyl)-2-amino-6,9-dihydro-1H-purin-6-one (IV), which is treated with POCl3 as before to yield the chloropurine (V). The dechlorination of (V) with HCO2H as before or with ammonium formate - Pd/C affords 9-(2-acetoxyethoxymethyl)-2-amino-9H-purine (VI), which is finally deacetylated with methylamine as before.
| 【1】 Stimac, A.; Kobe, J.; A new synthesis of acyclovir prodrugs. N2-Acetylacyclovir and 6-deoxya cyclovir. Synthesis 1990, 6, 6, 461-4. |
| 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) | 10784 | 2-[[2-(acetamido)-6-oxo-1,6-dihydro-9H-purin-9-yl]methoxy]ethyl acetate; Acetic acid 2-(2-acetamido-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester | 75128-73-3 | C12H15N5O5 | 详情 | 详情 |
| (II) | 10785 | 2-[[2-(acetamido)-6-chloro-9H-purin-9-yl]methoxy]ethyl acetate | C12H14ClN5O4 | 详情 | 详情 | |
| (III) | 10786 | 2-[[2-(acetamido)-9H-purin-9-yl]methoxy]ethyl acetate | C12H15N5O4 | 详情 | 详情 | |
| (IV) | 10787 | 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl acetate | C10H13N5O4 | 详情 | 详情 | |
| (V) | 10788 | 2-[(2-amino-6-chloro-9H-purin-9-yl)methoxy]ethyl acetate | C10H12ClN5O3 | 详情 | 详情 | |
| (VI) | 10789 | 2-[(2-amino-9H-purin-9-yl)methoxy]ethyl acetate | C10H13N5O3 | 详情 | 详情 |