6-Chloro-1,3-dimethyluracil; 6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】13978

【品名】6-Chloro-1,3-dimethyluracil; 6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

【CA登记号】6972-27-6

【分子式】C₆H₇ClN₂O₂

【分子量】174.58656

【元素组成】C 41.28% H 4.04% Cl 20.31% N 16.05% O 18.33%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

By condensation of N-(2-hydroxyethyl)-N-[3-(4-nitrophenyl)propyl]amine (I) with 1,3-dimethyl-6-[2-(p-toluenesulfonyloxy)ethylamino]pyrimidine-2,4(1H,3H)-dione (II) by means of NaOH in hot ethanol or methanol. The starting materials are obtained as follows: 1) The esterification of 3-(4-nitrophenyl)propanol (III) with p-toluenesulfonyl chloride (IV) by means of pyridine in chloroform gives the corresponding p-toluenesulfonate (V), which is then condensed with ethanolamine (VI) by heating at 100 C to afford amine (I). 2) The condensation of ethanolamine (VI) with 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VII) by heating at 90 C, or by means of triethylamine in refluxing isopropanol, gives 6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VIII), which is then esterified with p-toluenesulfonyl chloride (IV) as before yielding pyrimidine (II).

参考文献中间体

合成目标

【1】 Katakami, T.; Yokoyama, T.; Miyamoto, M.; Mori, H.; Kawauchi, N.; Nobori, T.; Sannohe, K.; Kamiya, J.; Ishii, M.; Yoshihara, K. (Mitsui Chemicals, Inc.); Pyrimidinedione deriv. cpds., method of producing the same and antiarrhythmic agents containing the same. AU 8943869; EP 0369627; JP 1991112948; JP 1991173873; US 5008267 .
【2】 Kaiho, T.; Mori, H.; Miyamoto, M.; Nobori, T.; Yokoyama, T.; Kawauchi, N.; Katakami, T.; San-nohe, K.; Synthesis and pharmacological studies of N-substituted 6-[(2-aminoethyl)amino]-1,3-dimethyl-2,4(1H,3H) pyrimidinediones, novel class III antiarrhythmic agents. J Med Chem 1992, 35, 18, 3325-30.
【3】 Castaner, J.; Prous, J.; MS-551. Drugs Fut 1993, 18, 3, 226.

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)	13972	2-[[3-(4-Nitrophenyl)propyl]amino]-1-ethanol		C₁₁H₁₆N₂O₃	详情	详情
(II)	13973	2-[(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)amino]ethyl 4-methylbenzenesulfonate		C₁₅H₁₉N₃O₅S	详情	详情
(III)	13974	3-(4-Nitrophenyl)-1-propanol		C₉H₁₁NO₃	详情	详情
(IV)	13975	p-Toluenesulfonyl chloride;p-tosyl chloride;Toluene-4-sulfonyl chloride;4-Toluene sulfochloride;tosyl chloride; 4-Methylbenzenesulfonyl chloride	98-59-9	C₇H₇ClO₂S	详情	详情
(V)	13976	3-(4-nitrophenyl)propyl 4-methylbenzenesulfonate		C₁₆H₁₇NO₅S	详情	详情
(VI)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(VII)	13978	6-Chloro-1,3-dimethyluracil; 6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione	6972-27-6	C₆H₇ClN₂O₂	详情	详情
(VIII)	13979	6-[(2-Hydroxyethyl)amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione		C₈H₁₃N₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Compound can be prepared in two different ways: 1) By condensation of o-methoxyphenylpiperazine carbonate (I) with 1,3-dimethyl-4-(3-chloropropylamino)uracil (II) in refluxing water. 2) By condensation of N-(o-methoxyphenyl)-N'-(3-aminopropyl)piperazine (III) with 1,3-dimethyl-4-chlorouracil (IV) in refluxing triethylamine.

参考文献中间体

合成目标

【1】 Pruesse, W.; et al.; Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production. FR 2073300; GB 1309324; US 3957786; US 4067982 .
【2】 Castaner, J.; Garcia-Rafanell, J.; Urapidil. Drugs Fut 1978, 3, 5, 397.

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)	11882	1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine	35386-24-4	C₁₁H₁₆N₂O	详情	详情
(II)	33441	6-[(3-chloropropyl)amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione		C₉H₁₄ClN₃O₂	详情	详情
(III)	33442	3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine; 3-[4-(2-methoxyphenyl)-1-piperazinyl]-1-propanamine		C₁₄H₂₃N₃O	详情	详情
(IV)	13978	6-Chloro-1,3-dimethyluracil; 6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione	6972-27-6	C₆H₇ClN₂O₂	详情	详情

Extended Information