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【结 构 式】 
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【分子编号】63396 【品名】4-({2-[2-ethyl-4-methyl-6-oxo-1(6H)-pyrimidinyl]ethyl}oxy)benzaldehyde 【CA登记号】 |
【 分 子 式 】C16H18N2O3 【 分 子 量 】286.3306 【元素组成】C 67.12% H 6.34% N 9.78% O 16.76% |
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：(III)2-Ethyl-6-methyl-3,4-dihydropyrimidin-4-one (I) is alkylated with 4-(2-bromoethoxy)benzaldehyde (II) in the presence of NaH and LiBr to afford (III). Subsequent Knoevenagel condensation of benzaldehyde (III) with thiazolidine-2,4-dione (IV) employing piperidine/benzoic acid leads to the benzylidene thiazolidinedione (V), which is finally reduced to the title benzyl thiazolidinedione by catalytic hydrogenation over Pd/C.
| 【1】 Madhavan, G.R.; Chakrabarti, R.; Vikramadithyan, R.K.; Mamidi, R.N.V.S.; Balraju, V.; Rajesh, B.M.; Misra, P.; Kumar, S.K.B.; Lohray, B.B.; Lohray, V.B.; Rajagopalan, R.; Synthesis and biological activity of novel pyrimidinone containing thiazolidinedione derivatives. Bioorg Med Chem 2002, 10, 8, 2671. |
| 【2】 Lohray, V.B.; Lohray, B.B.; Ramanujam, R.; Chakrabarti, R.; Gurram, R.M.; Paraselli, R.B.; Pakala, S.K.S. (Dr. Reddy's Research Foundation); Heterocyclic cpds., process for their preparation and pharmaceutical compsns. containing them and their use in the treatment of diabetes and related diseases. EP 0958296; US 5885997; US 5985884; US 6372750; US 6573268; WO 9741097 . |
| 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) | 63395 | 2-ethyl-6-methyl-4(3H)-pyrimidinone | C7H10N2O | 详情 | 详情 | |
| (II) | 18799 | 4-(2-bromoethoxy)benzaldehyde | 52191-15-8 | C9H9BrO2 | 详情 | 详情 |
| (III) | 63396 | 4-({2-[2-ethyl-4-methyl-6-oxo-1(6H)-pyrimidinyl]ethyl}oxy)benzaldehyde | C16H18N2O3 | 详情 | 详情 | |
| (IV) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (V) | 63397 | 5-{[4-({2-[2-ethyl-4-methyl-6-oxo-1(6H)-pyrimidinyl]ethyl}oxy)phenyl]methylidene}-1,3-thiazolidine-2,4-dione | C19H19N3O4S | 详情 | 详情 |
Extended Information