8-(4-bromophenyl)-6-[(2-hydroxyethyl)amino]-3-propyl-3,7-dihydro-2H-purin-2-one -Drug Synthesis Database

【结构式】

【分子编号】60211

【品名】8-(4-bromophenyl)-6-[(2-hydroxyethyl)amino]-3-propyl-3,7-dihydro-2H-purin-2-one

【CA登记号】

【分子式】C₁₆H₁₈BrN₅O₂

【分子量】392.25542

【元素组成】C 48.99% H 4.63% Br 20.37% N 17.85% O 8.16%

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：(VII)

The cyclization of 5,6-diamino-1-propylpyrimidine-2,4(1H,3H)-dione (I) with 4-bromobenzoic acid (II) by means of EDC and HOBT in DMF gives 8-(4-bromophenyl)-3-propylxanthine (III), which is treated with P2S5 in refluxing pyridine to yield the 6-thioxanthine (IV). The reaction of (IV) with Me-I and NaOH in ethanol affords the methylsulfanylpurin-2-one (V), which is treated with ethanolamine (VI) in DMSO at 150 C to provide the 2-hydroxyethylamino derivative (VII). Finally, this compound is cyclized by means of SOCl2 in refluxing chloroform to provide the target imidazopurine.

参考文献中间体

合成目标

【1】 Tsumuki, H.; Saki, M.; Nonaka, H.; Ichimura, M.; Shimada, J.; Suzuki, F.; Ichikawa, S.; Kosaka, N. (Kyowa Hakko Kogyo Co., Ltd.); Fused purine derivs.. EP 0884318; US 6306847; WO 9815555 .

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)	20546	5,6-diamino-1-propyl-2,4(1H,3H)-pyrimidinedione		C₇H₁₂N₄O₂	详情	详情
(II)	60207	4-bromo-1,3-cyclohexadiene-1-carboxylic acid		C₇H₇BrO₂	详情	详情
(III)	60208	8-(4-bromophenyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione		C₁₄H₁₃BrN₄O₂	详情	详情
(IV)	60209	8-(4-bromophenyl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one		C₁₄H₁₃BrN₄OS	详情	详情
(V)	60210	8-(4-bromophenyl)-6-(methylsulfanyl)-3-propyl-3,7-dihydro-2H-purin-2-one		C₁₅H₁₅BrN₄OS	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)	60211	8-(4-bromophenyl)-6-[(2-hydroxyethyl)amino]-3-propyl-3,7-dihydro-2H-purin-2-one		C₁₆H₁₈BrN₅O₂	详情	详情

Extended Information