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【结 构 式】

【分子编号】51572

【品名】4-[allyl(7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-butanol

【CA登记号】

【 分 子 式 】C25H34N4O

【 分 子 量 】406.57132

【元素组成】C 73.86% H 8.43% N 13.78% O 3.94%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

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:(V)

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
Extended Information