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【结 构 式】 
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【分子编号】38991 【品名】5-(5-pyrimidinylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone 【CA登记号】 |
【 分 子 式 】C9H8N4OS 【 分 子 量 】220.25488 【元素组成】C 49.08% H 3.66% N 25.44% O 7.26% S 14.56% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(VII)Palladium-catalyzed coupling of 5-bromopyrimidine (I) with ethyl acrylate (II) afforded pyrimidinyl acrylate (III), which was hydrogenated over Pd/C to give (IV). Claisen condensation of (IV) with ethyl formate furnished oxoester (V). This was then cyclized with thiourea (VI) to produce the intermediate thiouracil (VII).
| 【1】 Hickey, D.M.B.; Boyd, H.F.; Flynn, S.T.; et al.; 2-(Alkylthio)pyrimidin-4-ones as novel, reversible inhibitors of lipoprotein-associated phospholipase A2. Bioorg Med Chem Lett 2000, 10, 4, 395. |
| 【2】 Pinto, I.L.; Ife, R.J.; Hickey, D.M.B.; Smith, S.A.; Leach, C.A.; Porter, R.A. (SmithKline Beecham plc); Pyrimidinone cpds. and pharmaceutical compsns. containing them. EP 1028955; WO 9924420 . |
| 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) | 38987 | 5-bromopyrimidine | 4595-59-9 | C4H3BrN2 | 详情 | 详情 |
| (II) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (III) | 38988 | ethyl (E)-3-(5-pyrimidinyl)-2-propenoate | C9H10N2O2 | 详情 | 详情 | |
| (IV) | 38989 | ethyl 3-(5-pyrimidinyl)propanoate | C9H12N2O2 | 详情 | 详情 | |
| (V) | 38990 | ethyl (Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate | C10H12N2O3 | 详情 | 详情 | |
| (VI) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (VII) | 38991 | 5-(5-pyrimidinylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C9H8N4OS | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)Friedel-Crafts acylation of chlorobenzene (VIII) with 8-bromooctanoyl chloride (IX) in the presence of AlCl3 gave rise to bromo ketone (X). Finally, alkylation of thiouracil (VII) with bromoketone (X) generated the title compound.
| 【1】 Hickey, D.M.B.; Boyd, H.F.; Flynn, S.T.; et al.; 2-(Alkylthio)pyrimidin-4-ones as novel, reversible inhibitors of lipoprotein-associated phospholipase A2. Bioorg Med Chem Lett 2000, 10, 4, 395. |
| 【2】 Pinto, I.L.; Ife, R.J.; Hickey, D.M.B.; Smith, S.A.; Leach, C.A.; Porter, R.A. (SmithKline Beecham plc); Pyrimidinone cpds. and pharmaceutical compsns. containing them. EP 1028955; WO 9924420 . |
Extended Information