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【结 构 式】

【分子编号】63837

【品名】8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione

【CA登记号】

【 分 子 式 】C20H28N4O3

【 分 子 量 】372.46748

【元素组成】C 64.49% H 7.58% N 15.04% O 12.89%

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:M1

The oxidation of tricyclo[3.3.1.03,7]nonane-3-carboxylic acid methyl ester (I) with CrO3 in acetic anhydride/acetic acid gives a mixture of the 9-oxo and 6-oxo isomers (II), which is condensed with 5,6-diamino-1,3-dipropylpyrimidine-2,4(1H,3H)-dione (III) by means of LiOH, and after HPLC separation yields the 9-oxo isomer (IV) of the condensation product. The cyclization of (IV) by means of Ca(OH)2 affords the 1,3-dipropylxanthine derivative (V), which is finally reduced with LiBH4 to a mixture of isomers that is separated by HPLC yielding finally metabolite M1.

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
(IIb) 20542 methyl 6-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxylate C11H14O3 详情 详情
M1 63837 8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione C20H28N4O3 详情 详情
(I) 20540 methyl tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate C11H16O2 详情 详情
(III) 14628 5,6-diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione C10H18N4O2 详情 详情
(IV) 20544 N-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxamide 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

合成路线2

该中间体在本合成路线中的序号:M1

The selective biological hydroxylation of compounds (XII) by means of Absidia ramosa FERM BP-4605 in corn steep liquor, glucose, Brig 35 at 28 C, 5-7 days gives metabolites M1.

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
M1 63837 8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione C20H28N4O3 详情 详情
(XII) 20552 1,3-dipropyl-8-tricyclo[3.3.1.0(3,7)]non-3-yl-3,7-dihydro-1H-purine-2,6-dione C20H28N4O2 详情 详情
Extended Information