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【结 构 式】 
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【分子编号】36050 【品名】3-(6-chloro-9H-purin-9-yl)-2-nonanol 【CA登记号】 |
【 分 子 式 】C14H21ClN4O 【 分 子 量 】296.7998 【元素组成】C 56.66% H 7.13% Cl 11.94% N 18.88% O 5.39% |
合成路线1
该中间体在本合成路线中的序号：(VIII)This compound can be obtained by two related ways: 1) The condensation of 2-aminooctanoic acid (I) with acetic anhydride in pyridine at 100 C gives 3-acetamidononan-2-one (III), which is hydrolyzed with refluxing aqueous concentrated HCl yielding 3-aminononan-2-one hydrochloride (IV). The reduction of (IV) with NaBH4 in methanol affords 3-amino-2-nonanol (V), which is condensed with 4,6-dichloro-5-aminopyrimidine (VI) by means of tributylamine in refluxing pentanol giving 5-amino-6-(2-hydroxy-3-nonylamino)-4-chloropyrimidine (VII). The cyclization of (VII) with ethyl orthoformate (A) by means of ethanesulfonic acid in refluxing CHCl3 affords 9-(2-hydroxy-3-nonyl)-6-chloropurine (VIII), which is finally hydrolyzed with refluxing aqueous 0.5 N NaOH. 2) The chloropurine (VIII) is treated with methanolic NH3 at 80-100 C in a pressure vessel to give 9-(2-hydroxy-3-nonyl)adenine (IX), which is then treated with NaNO2 in acetic acid aqueous HCl.
| 【1】 Giner-Sorolla, A. (Newport Pharmaceuticals International Inc.; Sloan-Kettering Institute); 9-(Hydroxy alkyl)purines. US 4221910 . |
| 【2】 Simon, L.N.; Hadden, J.W. (Newport Pharmaceuticals International Inc.; Sloan-Kettering Institute); Method of imparting immunomodulating and antiviral activity. US 4221794 . |
| 【3】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Arrigoni-Martelli, E.; NPT-15,392. Drugs Fut 1983, 8, 5, 420. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 21304 | Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether | 122-51-0 | C7H16O3 | 详情 | 详情 |
| (I) | 36045 | 2-aminooctanoic acid | C8H17NO2 | 详情 | 详情 | |
| (III) | 36046 | N-(1-acetylheptyl)acetamide | C11H21NO2 | 详情 | 详情 | |
| (IV) | 36047 | 3-amino-2-nonanone | C9H19NO | 详情 | 详情 | |
| (V) | 36048 | 3-amino-2-nonanol | C9H21NO | 详情 | 详情 | |
| (VI) | 22845 | 5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine | 5413-85-4 | C4H3Cl2N3 | 详情 | 详情 |
| (VII) | 36049 | 3-[(5-amino-6-chloro-4-pyrimidinyl)amino]-2-nonanol | C13H23ClN4O | 详情 | 详情 | |
| (VIII) | 36050 | 3-(6-chloro-9H-purin-9-yl)-2-nonanol | C14H21ClN4O | 详情 | 详情 | |
| (IX) | 36051 | 3-(6-amino-9H-purin-9-yl)-2-nonanol | C14H23N5O | 详情 | 详情 |