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【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.

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