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【结 构 式】 
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【分子编号】57055 【品名】4-Phenoxyphenylboronic acid 【CA登记号】51067-38-0 |
【 分 子 式 】C12H11BO3 【 分 子 量 】214.02854 【元素组成】C 67.34% H 5.18% B 5.05% O 22.43% |
合成路线1
该中间体在本合成路线中的序号：(IX)In an alternative synthetic route, cyclization of the aminopyrazole (I) with formamide gives the pyrazolopyrimidine (II), which is then iodinated to (III) by means of N-iodosuccinimide. Mitsunobu coupling of (III) with 4,4-(ethylenedioxy)cyclohexanol (IV) produces the cyclohexyl pyrazolopyrimidine derivative (V), and further ketal hydrolysis leads to ketone (VI). This is subjected to reductive amination with N-methylpiperazine (VII) in the presence of NaBH(OAc)3 to yield (VIII). Finally, Suzuki coupling of iodopyrazolopyrimidine (VIII) with 4-phenoxyphenylboronic acid (IX) gives rise to the title compound.
| 【1】 Burchat, A.F.; et al.; Pyrazolo[3,4-d]pyrimidines containing an extended 3-substituent as potent inhibitors of Lck - A selective insight. Bioorg Med Chem Lett 2002, 12, 12, 1687. |
| 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) | 57051 | 5-Amino-4-pyrazolecarbonitrile | C4H4N4 | 详情 | 详情 | |
| (II) | 41249 | 4-amine-1H-pyrazolo[3,4-d]pyrimidine; 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine; 1H-pyrazolo[3,4-d]pyrimidin-4-amine | 2380-63-4 | C5H5N5 | 详情 | 详情 |
| (III) | 41250 | 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine | C5H4IN5 | 详情 | 详情 | |
| (IV) | 53564 | 1,4-dioxaspiro[4.5]decan-8-ol | 22428-87-1 | C8H14O3 | 详情 | 详情 |
| (V) | 57052 | 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine; 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | C13H16IN5O2 | 详情 | 详情 | |
| (VI) | 57053 | 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone | C11H12IN5O | 详情 | 详情 | |
| (VII) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (VIII) | 57054 | 3-iodo-1-[4-(4-methyl-1-piperazinyl)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-iodo-1-[4-(4-methyl-1-piperazinyl)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine | C16H24IN7 | 详情 | 详情 | |
| (IX) | 57055 | 4-Phenoxyphenylboronic acid | 51067-38-0 | C12H11BO3 | 详情 | 详情 |