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【结 构 式】 
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【分子编号】40641 【品名】3-iodo-4,5-dimethoxybenzaldehyde 【CA登记号】32024-15-0 |
【 分 子 式 】C9H9IO3 【 分 子 量 】292.07313 【元素组成】C 37.01% H 3.11% I 43.45% O 16.43% |
合成路线1
该中间体在本合成路线中的序号：(II)Methylation of 5-iodovanillin (I) with dimethyl sulfate and K2CO3 afforded dimethoxy derivative (II). This was condensed with 3-anilinopropionitrile (III) in the presence of potassium tert-butoxide yielding the enamino nitrile (IV). Subsequent cyclization of (IV) with guanidine hydrochloride (V) produced diaminopyrimidine (VI).
| 【1】 Guerry, P.; Locher, H.H.; Hubschwerlen, C.; Wyss, P.C.; Jolidon, S.; Hartman, P.G.; Stalder, H.; Specklin, J.L.; Anti-MRSA dihydrofolate reductase inhibitors: Synthesis and SAR. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F1800. |
| 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) | 12758 | 4-Hydroxy-3-iodo-5-methoxybenzaldehyde; 5-Iodovanillin | 5438-36-8 | C8H7IO3 | 详情 | 详情 |
| (II) | 40641 | 3-iodo-4,5-dimethoxybenzaldehyde | 32024-15-0 | C9H9IO3 | 详情 | 详情 |
| (III) | 27195 | 3-anilinopropanenitrile | 1075-76-9 | C9H10N2 | 详情 | 详情 |
| (IV) | 40642 | (Z)-3-anilino-2-(3-iodo-4,5-dimethoxybenzyl)-2-propenenitrile | C18H17IN2O2 | 详情 | 详情 | |
| (V) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |
| (VI) | 40643 | 5-(3-iodo-4,5-dimethoxybenzyl)-2,4-pyrimidinediamine; 2-amino-5-(3-iodo-4,5-dimethoxybenzyl)-4-pyrimidinylamine | C13H15IN4O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Methylation of 5-iodovanillin (I) with dimethyl sulfate and K2CO3 afforded dimethoxy derivative (II). This was condensed with 3-anilinopropionitrile (III) in the presence of potassium tert-butoxide yielding the enamino nitrile (IV). Subsequent cyclization of (IV) with guanidine hydrochloride (V) produced diaminopyrimidine (VI). Cinnamate derivative (VIII) was then obtained by palladium-catalyzed coupling of (VI) with ethyl acrylate (VII).
| 【1】 Guerry, P.; Locher, H.H.; Hubschwerlen, C.; Wyss, P.C.; Jolidon, S.; Hartman, P.G.; Stalder, H.; Specklin, J.L.; Anti-MRSA dihydrofolate reductase inhibitors: Synthesis and SAR. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F1800. |
| 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) | 12758 | 4-Hydroxy-3-iodo-5-methoxybenzaldehyde; 5-Iodovanillin | 5438-36-8 | C8H7IO3 | 详情 | 详情 |
| (II) | 40641 | 3-iodo-4,5-dimethoxybenzaldehyde | 32024-15-0 | C9H9IO3 | 详情 | 详情 |
| (III) | 27195 | 3-anilinopropanenitrile | 1075-76-9 | C9H10N2 | 详情 | 详情 |
| (IV) | 40642 | (Z)-3-anilino-2-(3-iodo-4,5-dimethoxybenzyl)-2-propenenitrile | C18H17IN2O2 | 详情 | 详情 | |
| (V) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |
| (VI) | 40643 | 5-(3-iodo-4,5-dimethoxybenzyl)-2,4-pyrimidinediamine; 2-amino-5-(3-iodo-4,5-dimethoxybenzyl)-4-pyrimidinylamine | C13H15IN4O2 | 详情 | 详情 | |
| (VII) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (VIII) | 40649 | ethyl (E)-3-[5-[(2,4-diamino-5-pyrimidinyl)methyl]-2,3-dimethoxyphenyl]-2-propenoate | C18H22N4O4 | 详情 | 详情 |