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【结 构 式】 
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【分子编号】51573 【品名】N-allyl-N-(4-fluorobutyl)-N-(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine; N-allyl-N-(4-fluorobutyl)-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 【CA登记号】 |
【 分 子 式 】C25H33FN4 【 分 子 量 】408.5623832 【元素组成】C 73.5% H 8.14% F 4.65% N 13.71% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 4-chloro-1-butanol (I) with allylamine (II) by means of K2CO3 in refluxing THF gives N-allyl-N-(4-hydroxybutyl)amine (III), which is condensed with the pyrrolo[2,3-d]pyrimidine derivative (IV) by heating at 130 C in DMSO to afford the tertiary amine (V). The reaction of (V) with TBAF and Ts-F in THF provides the 4-fluorobutyl derivative (VI). Finally, the hydrogenation of the allylic double bond of (VI) with H2 over Pd/C in ethanol gives the target LWH-154.
| 【1】 Gold, P.W.; Contoreggi, C.; Webster, E.L.; Eckelman, W.C.; Rice, K.C.; Hsin, L.-W.; Chrousos, G.P.; Synthesis of [3H] (4-fluorobutyl)propyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amine: A potent radioligand for corticotropin-releasing hormone type 1 receptor. J Label Compd Radiopharm 2000, 43, 9, 899. |
| 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) | 22336 | 4-chloro-1-butanol | 928-51-8 | C4H9ClO | 详情 | 详情 |
| (II) | 13672 | Allylamine; 2-Propen-1-amine | 107-11-9 | C3H7N | 详情 | 详情 |
| (III) | 51571 | 4-(allylamino)-1-butanol | C7H15NO | 详情 | 详情 | |
| (IV) | 45880 | 4-chloro-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine | C18H20ClN3 | 详情 | 详情 | |
| (V) | 51572 | 4-[allyl(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-butanol | C25H34N4O | 详情 | 详情 | |
| (VI) | 51573 | N-allyl-N-(4-fluorobutyl)-N-(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine; N-allyl-N-(4-fluorobutyl)-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C25H33FN4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The reaction of 4-chloro-1-butanol (I) with allylamine (II) by means of K2CO3 in refluxing THF gives N-allyl-N-(4-hydroxybutyl)amine (III), which is condensed with the pyrrolo[2,3-d]pyrimidine derivative (IV) by heating at 130 C in DMSO to afford the tertiary amine (V). The reaction of (V) with TBAF and Ts-F in THF provides the 4-fluorobutyl derivative (VI). Finally, the hydrogenation of the allylic double bond of (VI) with 3H2 over Pd/C in ethanol gives the target tritium-labeled LWH-154.
| 【1】 Gold, P.W.; Contoreggi, C.; Webster, E.L.; Eckelman, W.C.; Rice, K.C.; Hsin, L.-W.; Chrousos, G.P.; Synthesis of [3H] (4-fluorobutyl)propyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amine: A potent radioligand for corticotropin-releasing hormone type 1 receptor. J Label Compd Radiopharm 2000, 43, 9, 899. |
| 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) | 22336 | 4-chloro-1-butanol | 928-51-8 | C4H9ClO | 详情 | 详情 |
| (II) | 13672 | Allylamine; 2-Propen-1-amine | 107-11-9 | C3H7N | 详情 | 详情 |
| (III) | 51571 | 4-(allylamino)-1-butanol | C7H15NO | 详情 | 详情 | |
| (IV) | 45880 | 4-chloro-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine | C18H20ClN3 | 详情 | 详情 | |
| (V) | 51572 | 4-[allyl(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-butanol | C25H34N4O | 详情 | 详情 | |
| (VI) | 51573 | N-allyl-N-(4-fluorobutyl)-N-(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine; N-allyl-N-(4-fluorobutyl)-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C25H33FN4 | 详情 | 详情 |