N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】20548

【品名】N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide

【CA登记号】

【分子式】C₁₇H₂₄N₄O₄

【分子量】348.40212

【元素组成】C 58.61% H 6.94% N 16.08% O 18.37%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VIII)

The condensation of 9-oxotricyclo[3.3.1.03,7]nonane-3-carboxylic acid methyl ester (II) with 5,6-diamino-1-propylpyrimidine-2,4(1H,3H)-dione (VI) by means of LiOH gives the expected condensation product (VII), which by reduction with NaBH4 and HPLC separation yields the exo-hydroxy isomer (VIII). The condensation of (VIII) with bromoacetone (IX) by means of cesium carbonate affords compound (X), which is cyclized with Ca(OH)2 as before to give metabolite M3. Finally, this compound is reduced with NaBH4 to afford metabolite M2.

参考文献中间体

合成目标

【1】 Shimada, J.; Eguchi, T.; Yasuzawa, T.; Nakamura, A.; Horiguchi, A.; Mochida, K.; Suzuki, F.; Synthesis of rat metabolites of a adenosine A1 antagonist, KW-3902. Symp Med Chem 1996, Abst 1-P-24.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IIa)	20541	methyl 9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxylate		C₁₁H₁₄O₃	详情	详情
M3	63838	8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1-(2-oxopropyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione		C₂₀H₂₆N₄O₄	详情	详情
M2	63839	1-(2-hydroxypropyl)-8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione		C₂₀H₂₈N₄O₄	详情	详情
(V)	20545	8-(9-oxotricyclo[3.3.1.0(3,7)]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione		C₂₀H₂₆N₄O₃	详情	详情
(VI)	20546	5,6-diamino-1-propyl-2,4(1H,3H)-pyrimidinedione		C₇H₁₂N₄O₂	详情	详情
(VII)	20547	N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxamide		C₁₇H₂₂N₄O₄	详情	详情
(VIII)	20548	N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide		C₁₇H₂₄N₄O₄	详情	详情
(IX)	20549	1-bromoacetone	598-31-2	C₃H₅BrO	详情	详情
(X)	20550	N-[6-amino-2,4-dioxo-3-(2-oxopropyl)-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl]-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide		C₂₀H₂₈N₄O₅	详情	详情

Extended Information