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【结 构 式】 
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【分子编号】52898 【品名】4(5)-Amino-1H-imidazole-5(4)-carbonitrile; 4(5)-Amino-5(4)-cyanoimidazole 【CA登记号】5098-11-3 |
【 分 子 式 】C4H4N4 【 分 子 量 】108.10272 【元素组成】C 44.44% H 3.73% N 51.83% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 4-amino-1H-imidazole-5-carbonitrile (I) with trimethyl orthopentanoate (II) in hot DMF gives methyl N-(5-cyano-1H-imidazol-4-yl)pentanoimidate (III), which is then cyclized with benzoic hydrazide (IV) in hot DMF to yield the target triazolo-purine derivative.
| 【1】 Kurogi, Y.; Nishikawa, H.; Okamura, T. (Otsuka Pharmaceutical Co., Ltd.); Triazolopurine derivs, medicinal compsn. containing the derivs., adenosine A3 receptor compatibilizing agent, and asthmatic remedy. EP 1069126; US 6288070; WO 9951606 . |
| 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) | 52898 | 4(5)-Amino-1H-imidazole-5(4)-carbonitrile; 4(5)-Amino-5(4)-cyanoimidazole | 5098-11-3 | C4H4N4 | 详情 | 详情 |
| (II) | 57416 | 1,1,1-Trimethoxy-n-pentane; 1,1,1-Trimethoxypentane; ortho-N-Valeric acid trimethyl ester; Trimethyl orthovalerate | 13820-09-2 | C8H18O3 | 详情 | 详情 |
| (III) | 57417 | methyl N-(5-cyano-1H-imidazol-4-yl)pentanimidoate | C10H14N4O | 详情 | 详情 | |
| (IV) | 57418 | 4-(Trifluoromethyl)benzhydrazide; 4-(Trifluoromethyl)benzoic acid hydrazide; alpha,alpha,alpha-Trifluoro-p-toluic acid hydrazide | 339-59-3 | C8H7F3N2O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Condensation of 4-amino-5-cyanoimidazole (I) with pentanamide (II) upon heating at 210 C produced the 2-butyladenine (III). Subsequent alkylation of (III) with 4-fluorobenzyl chloride (IV) yielded the 9-fluorobenzyl adenine (V). This was brominated at position 8 using Br2 and NaOAc in HOAc. The resultant 8-bromo adenine (VI) was finally hydrolyzed under acidic conditions to the title 8-hydroxy derivative.
| 【1】 Matsui, H.; Takaku, H.; Isobe, Y.; Ogita, H.; Tobe, M.; Tomizawa, H. (Japan Energy Corp.); Type 2 helper T cell-selective immune response suppressors. EP 1043021; US 6376501; WO 9932122 . |
| 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) | 52898 | 4(5)-Amino-1H-imidazole-5(4)-carbonitrile; 4(5)-Amino-5(4)-cyanoimidazole | 5098-11-3 | C4H4N4 | 详情 | 详情 |
| (II) | 52899 | Pentanamide; Valeramide; n-Valeramide | 626-97-1 | C5H11NO | 详情 | 详情 |
| (III) | 52900 | 2-butyl-9H-purin-6-amine; 2-butyl-9H-purin-6-ylamine | C9H13N5 | 详情 | 详情 | |
| (IV) | 12354 | 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene | 352-11-4 | C7H6ClF | 详情 | 详情 |
| (V) | 52901 | 2-butyl-9-(4-fluorobenzyl)-9H-purin-6-amine; 2-butyl-9-(4-fluorobenzyl)-9H-purin-6-ylamine | C16H18FN5 | 详情 | 详情 | |
| (VI) | 52902 | 8-bromo-2-butyl-9-(4-fluorobenzyl)-9H-purin-6-ylamine; 8-bromo-2-butyl-9-(4-fluorobenzyl)-9H-purin-6-amine | C16H17BrFN5 | 详情 | 详情 |