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【结 构 式】 
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【分子编号】60209 【品名】8-(4-bromophenyl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one 【CA登记号】 |
【 分 子 式 】C14H13BrN4OS 【 分 子 量 】365.25358 【元素组成】C 46.04% H 3.59% Br 21.88% N 15.34% O 4.38% S 8.78% |
合成路线1
该中间体在本合成路线中的序号：(IV)The cyclization of 5,6-diamino-1-propylpyrimidine-2,4(1H,3H)-dione (I) with 4-bromobenzoic acid (II) by means of EDC and HOBT in DMF gives 8-(4-bromophenyl)-3-propylxanthine (III), which is treated with P2S5 in refluxing pyridine to yield the 6-thioxanthine (IV). The reaction of (IV) with Me-I and NaOH in ethanol affords the methylsulfanylpurin-2-one (V), which is treated with ethanolamine (VI) in DMSO at 150 C to provide the 2-hydroxyethylamino derivative (VII). Finally, this compound is cyclized by means of SOCl2 in refluxing chloroform to provide the target imidazopurine.
| 【1】 Tsumuki, H.; Saki, M.; Nonaka, H.; Ichimura, M.; Shimada, J.; Suzuki, F.; Ichikawa, S.; Kosaka, N. (Kyowa Hakko Kogyo Co., Ltd.); Fused purine derivs.. EP 0884318; US 6306847; WO 9815555 . |
| 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) | 20546 | 5,6-diamino-1-propyl-2,4(1H,3H)-pyrimidinedione | C7H12N4O2 | 详情 | 详情 | |
| (II) | 60207 | 4-bromo-1,3-cyclohexadiene-1-carboxylic acid | C7H7BrO2 | 详情 | 详情 | |
| (III) | 60208 | 8-(4-bromophenyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione | C14H13BrN4O2 | 详情 | 详情 | |
| (IV) | 60209 | 8-(4-bromophenyl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one | C14H13BrN4OS | 详情 | 详情 | |
| (V) | 60210 | 8-(4-bromophenyl)-6-(methylsulfanyl)-3-propyl-3,7-dihydro-2H-purin-2-one | C15H15BrN4OS | 详情 | 详情 | |
| (VI) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (VII) | 60211 | 8-(4-bromophenyl)-6-[(2-hydroxyethyl)amino]-3-propyl-3,7-dihydro-2H-purin-2-one | C16H18BrN5O2 | 详情 | 详情 |