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【结 构 式】

【分子编号】26031

【品名】4-chloro-5-iodo-2,6-dimethylpyrimidine

【CA登记号】

【 分 子 式 】C6H6ClIN2

【 分 子 量 】268.48429

【元素组成】C 26.84% H 2.25% Cl 13.2% I 47.27% N 10.43%

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)

3) The iodination of 2,6-dimethylpyrimidin-4-ol (IX) with I2/NaOH in refluxing water gives 5-iodo-2,6-dimethylpyrimidin-4-ol (X), which is treated with POCl3 in refluxig toluene yielding 4-chloro-5-iodo-2,6-dimethylpyrimidine (XI). The reaction of (XI) with (1-ethoxyvinyl)tributyltin (XII) catalyzed by tetrakis(triphenylphosphine)palladium in refluxing dioxane affords 4-chloro-5-(1-ethoxyvinyl)-2,6-dimethylpyrimidine (XIII), which is condensed with 4-bromobenzylamine (XIV) by means of NaHCO3 in refluxing butanol giving 4-(4-bromobenzylamino)-5-(1-ethoxyvinyl)-2,6-dimethylpyrimidine (XV). The hydrolysis of (XV) with HCl in refluxing acetone yields the corresponding acetyl derivative (XVI), which is condensed with 2-(2-tert-butyl-2H-tetrazol-5-yl)phenylboronic acid (XVII) by means of tetrakis(triphenylphosphine)palladium to afford the biphenyl derivative (XVIII). The cyclization of (XVIII) with diethyl carbonate and NaH in hot THF gives 8-[2'-(2-tert-butyl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5-hydroxy-2,4-dimethylpyrido[2,3-d]pyrimidin-7(8H)-one (XIX), which is finally deprotected with trifluoromethanesulfonic acid in refluxing toluene to give metabolite (III).

1 Ellingboe, J.W.; Collini, M.D.; Quagliato, D.; Chen, J.; Antane, M.; Schmid, J.; Hartupee, D.; White, V.; Park, C.H.; Tanikella, T.; Bagli, J.F.; Metabolites of the angiotensin II antagonist tasosartan: The importance of a second acidic group. J Med Chem 1998, 41, 22, 4251.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 26028 5-hydroxy-2,4-dimethyl-8-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]pyrido[2,3-d]pyrimidin-7(8H)-one C23H19N7O2 详情 详情
(IX) 26029 2,6-dimethyl-4-pyrimidinol 6622-92-0 C6H8N2O 详情 详情
(X) 26030 5-iodo-2,6-dimethyl-4-pyrimidinol C6H7IN2O 详情 详情
(XI) 26031 4-chloro-5-iodo-2,6-dimethylpyrimidine C6H6ClIN2 详情 详情
(XII) 19760 ethyl 1-(tributylstannyl)vinyl ether; tributyl(1-ethoxyvinyl)stannane 97674-02-7 C16H34OSn 详情 详情
(XIII) 26032 1-(4-chloro-2,6-dimethyl-5-pyrimidinyl)vinyl ethyl ether; 4-chloro-5-(1-ethoxyvinyl)-2,6-dimethylpyrimidine C10H13ClN2O 详情 详情
(XIV) 15869 4-bromobenzylamine; (4-bromophenyl)methanamine 26177-44-6 C7H8BrN 详情 详情
(XV) 26033 N-(4-bromobenzyl)-5-(1-ethoxyvinyl)-2,6-dimethyl-4-pyrimidinamine; N-(4-bromobenzyl)-N-[5-(1-ethoxyvinyl)-2,6-dimethyl-4-pyrimidinyl]amine C17H20BrN3O 详情 详情
(XVI) 26034 1-[4-[(4-bromobenzyl)amino]-2,6-dimethyl-5-pyrimidinyl]-1-ethanone C15H16BrN3O 详情 详情
(XVII) 15871 2-[2-(tert-butyl)-2H-1,2,3,4-tetraazol-5-yl]phenylboronic acid C11H15BN4O2 详情 详情
(XVIII) 26035 1-[4-[([2'-[2-(tert-butyl)-2H-1,2,3,4-tetraazol-5-yl][1,1'-biphenyl]-4-yl]methyl)amino]-2,6-dimethyl-5-pyrimidinyl]-1-ethanone C26H29N7O 详情 详情
(XIX) 26036 8-([2'-[2-(tert-butyl)-2H-1,2,3,4-tetraazol-5-yl][1,1'-biphenyl]-4-yl]methyl)-5-hydroxy-2,4-dimethylpyrido[2,3-d]pyrimidin-7(8H)-one C27H27N7O2 详情 详情
Extended Information