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【结 构 式】 
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【分子编号】36163 【品名】9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid 【CA登记号】 |
【 分 子 式 】C10H10Br2N2O3 【 分 子 量 】366.00908 【元素组成】C 32.82% H 2.75% Br 43.66% N 7.65% O 13.11% |
合成路线1
该中间体在本合成路线中的序号：(I)This compound can be obtained by several different ways: 1) By condensation of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (I) with phenylhydrazine (II) by means of N,N-dimethylaniline in DMSO. 2) By a coupling reaction between 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid (III) with phenyldiazonium chloride (IV) (prepared with aniline (V), NaNO2 and HCl). 3) The coupling reaction of (IV) with ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine 3-carboxylate (VI) gives ethyl 6-methyl-4-oxo-9-(phenylhydrazono)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (VII), which is hydrolyzed with NaOH in water. 4) By reaction of ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (VIII) with (II) in refluxing ethanol, giving (VII), already obtained. 5) By condensation of ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate (IX) with (II) in refluxing ethanol yielding (VII), already obtained.
| 【1】 Vasvari-Debreczy, L.; Horvath, A.; Dessy, F.; Hermecz, I.; De Vos, C.; Meszaros, Z.; Rodriguez, L.; Breining, T.; 18. New antiallergic 4H-pyridol[1,2-a]pyrimidin-4-ones. J Med Chem 1982, 25, 10, 1140-45. |
| 【2】 Bitter, I.; Breining, T.; Mandi, A.; Szucs, T.; Horvath, A.; Meszaros, Z.; Virag, S.; Hermecz, I.; Vasvari, L.; Nagy, G.; Sebestyen, G. (Chinoin Pharmaceutical and Chemical Works Co., Ltd.); Condensed pyrimidine derivs., their preparation and pharmaceutical compsns. containing them. GB 2011898 . |
| 【3】 Vasvari, L.; Horvath, A.; Hermecz, I.; Kokosi, J.; Breining, T. (Chinoin Pharmaceutical and Chemical Works Co., Ltd.); 9-Hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]-pyrimidine-4-one derivs., their preparation and pharmaceutical compsns. containing them. GB 2051783 . |
| 【4】 Castaner, J.; Serradell, M.N.; Sneddon, J.M.; Blancafort, P.; UCB-L-140. Drugs Fut 1983, 8, 7, 612. |
| 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) | 36163 | 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid | C10H10Br2N2O3 | 详情 | 详情 | |
| (II) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |
| (III) | 36162 | 6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid | C10H12N2O3 | 详情 | 详情 | |
| (IV) | 25897 | benzenediazonium chloride | C6H5ClN2 | 详情 | 详情 | |
| (V) | 12294 | Aniline; Phenylamine | 62-53-3 | C6H7N | 详情 | 详情 |
| (VI) | 36161 | ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate | C12H16N2O3 | 详情 | 详情 | |
| (VII) | 36160 | ethyl 6-methyl-4-oxo-9-[(Z)-2-phenylhydrazono]-7,8-dihydro-4H-pyrido[1,2-a]pyrimidine-3(6H)-carboxylate | C18H20N4O3 | 详情 | 详情 | |
| (VIII) | 36158 | ethyl 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate | C12H15BrN2O3 | 详情 | 详情 | |
| (IX) | 36159 | ethyl 9-hydroxy-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate | C12H16N2O4 | 详情 | 详情 |