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【结 构 式】

【分子编号】51904

【品名】1,9-dihydro-6H-purin-6-one

【CA登记号】

【 分 子 式 】C5H4N4O

【 分 子 量 】136.11312

【元素组成】C 44.12% H 2.96% N 41.16% O 11.75%

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:(XI)

The esterification of 1H-imidazole-4,5-dicarboxylic acid (I) with EtOH and sulfuric acid gives the diethyl ester (II), which is brominated with NBS in acetonitrile, yielding the 2-bromo derivative (III). The hydrolysis of (III) by means of hot aqueous Na2CO3 affords the 2-bromo-1H-imidazole-4,5-dicarboxylic acid (IV), which is diazocoupled with the labeled diazonium ion (V) to provide the monolabeled azo acid (VI). The reaction of acid (VI) with 15NH4Cl and DEC in acetonitrile gives the doubly labeled azoamide (VII), which is reduced with H2 over Pd/C in methanol to yield the doubly labeled 5-amino-1H-imidazole-4-carboxamide (VIII). The cyclization of (VIII) with sodium 13C-ethylxanthate (IX) in DMF affords the mercaptoxanthine (X), which is reduced to the hypoxanthine (XI) with Raney Ni and formic acid. The reaction of (XI) with POCl3 in hot N,N-dimethylaniline provides the triply labeled chloropurine (XII), which is submitted to enzymatic trans-glycosylation with 7-methylguanosine or thymidine and purine nucleoside phosphorylase (PNP) and thymidine phosphorylase (TP) to give the glycosylated chloropurine (XIII). Finally, this compound is treated with 15NH4Cl and KHCO3 in hot anhydrous DMSO to afford the target tetralabeled adenine nucleoside.

1 Abad, J.-L.; Gaffney B.L.; Jones R.A.; 15N-multilabeled adenine and guanine nucleosides syntheses of [1,3,NH2-15N3]- and [2-13C-1,3NH2-15N3]-labeled adenosine, guanosine , 2'-deoxyadenosine, and 2'-deoxyguanosine. J Org Chem 1999, 64, 18, 6575.
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) 31951 1H-imidazole-4,5-dicarboxylic acid 570-22-9 C5H4N2O4 详情 详情
(II) 27424 3-(1-trityl-1H-imidazol-4-yl)-1-propanol C25H24N2O 详情 详情
(III) 51896 diethyl 2-bromo-1H-imidazole-4,5-dicarboxylate C9H11BrN2O4 详情 详情
(IV) 51897 2-bromo-1H-imidazole-4,5-dicarboxylic acid C5H3BrN2O4 详情 详情
(V) 51898 4-bromobenzenediazonium C6H4BrN2 详情 详情
(V) 51907 4-bromobenzenediazonium C6H4BrN2 详情 详情
(VI) 51899 2-bromo-5-[(E)-2-phenyldiazenyl]-1H-imidazole-4-carboxylic acid C10H7BrN4O2 详情 详情
(VI) 51908 2-bromo-5-[(E)-2-phenyldiazenyl]-1H-imidazole-4-carboxylic acid C10H7BrN4O2 详情 详情
(VII) 51900 2-bromo-5-[(E)-2-phenyldiazenyl]-1H-imidazole-4-carboxamide C10H8BrN5O 详情 详情
(VII) 51909 2-bromo-5-[(E)-2-phenyldiazenyl]-1H-imidazole-4-carboxamide C10H8BrN5O 详情 详情
(VIII) 11015 5-Amino-1H-imidazole-4-carboxamide 360-97-4 C4H6N4O 详情 详情
(VIII) 51901 5-amino-1H-imidazole-4-carboxamide C4H6N4O 详情 详情
(IX) 51902   C3H5NaOS2 详情 详情
(IX) 51910   C3H5NaOS2 详情 详情
(X) 51903   C5H3N4NaOS 详情 详情
(X) 51911   C5H3N4NaOS 详情 详情
(XI) 51904 1,9-dihydro-6H-purin-6-one C5H4N4O 详情 详情
(XI) 51912 1,9-dihydro-6H-purin-6-one C5H4N4O 详情 详情
(XII) 17692 6-Chloropurine; 6-chloro-9H-purine 87-42-3 C5H3ClN4 详情 详情
(XII) 51905 6-chloro-9H-purine C5H3ClN4 详情 详情
(XIII) 18716 6-chloropurine riboside; (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol 2004-06-0 C10H11ClN4O4 详情 详情
(XIII) 51906 (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol C10H11ClN4O4 详情 详情
Extended Information