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【结 构 式】 
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【药物名称】 【化学名称】N-(2-Butylthieno[3,2-d]pyrimidin-4-yl)-N-cyclohexylamine hydrochloride 【CA登记号】214416-93-0 【 分 子 式 】C16H24ClN3S 【 分 子 量 】325.90678 |
【开发单位】Almirall Prodesfarma (Originator) 【药理作用】Asthma Therapy, Bronchodilators, RESPIRATORY DRUGS, Phosphodiesterase IV Inhibitors |
合成路线1
This compound can be obtained by several related ways: 1.- The cyclization of 3-aminothiophene-2-carboxamide (I) with pentanoyl anhydride (II) by means of DCC, DMAP and pyridine in DMF and NaOH gives 2-butylthieno[3,2-d]pyrimidin-4(3H)-one (III), which by reaction with POCl3 or SOCl2 affords 2-butyl-4-chlorothieno[3,2-d]pyrimidine (IV). Finally, this compound is condensed with cyclohexylamine (V) by means of triethylamine in in THF. 2.- The intermediate 2-butylthieno[3,2-d]pyrimidin-4-(3H)-one (III) can be obtained by other ways: a.- By cyclization of amide (I) with pentanoic acid (VI) by means of DCC, DMAP and pyridine in DMF and NaOH. b.- By cyclization of 3-aminothiophene-2-carboxylic acid methyl ester (VII) with pentanoic acid (VI) by means of DCC, DMAP and ammonia in dichloromethane. c.- By cyclization of 3-aminothiophene-2-carboxylic acid methyl ester (VII) with pentanoyl chloride (VIII) by means of pyridine and ammonia. d.- By cyclization of 3-aminothiophene-2-carboxylic acid (IX) with pentanoic anhydride (II) and ammonia.
| 【1】 Crespo, M. I.; Pages, L.; Vega, A.; Segarra, V.; Lopez, M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J.M.; Design, synthesis, and biological activities of new thieno[3,2-d]pyrimidines as selective type 4 phosphodiesterase inhibitors. J Med Chem 1998, 41, 21, 4021. |
| 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) | 27682 | 3-amino-2-thiophenecarboxamide | 147123-47-5 | C5H6N2OS | 详情 | 详情 |
| (II) | 27683 | pentanoic anhydride | 2082-59-9 | C10H18O3 | 详情 | 详情 |
| (III) | 27684 | 2-butylthieno[3,2-d]pyrimidin-4(3H)-one | C10H12N2OS | 详情 | 详情 | |
| (IV) | 27685 | 2-butyl-4-chlorothieno[3,2-d]pyrimidine | C10H11ClN2S | 详情 | 详情 | |
| (V) | 17966 | cyclohexanamine; cyclohexyl amine; cyclohexylamine | 108-91-8 | C6H13N | 详情 | 详情 |
| (VI) | 19682 | pentanoic acid | 109-52-4 | C5H10O2 | 详情 | 详情 |
| (VII) | 27686 | 3-amino-2-thiophenecarboxylic acid methyl ester; methyl 3-amino-2-thiophenecarboxylate | 22288-78-4 | C6H7NO2S | 详情 | 详情 |
| (VIII) | 15116 | pentanoyl chloride; valeryl chloride | 638-29-9 | C5H9ClO | 详情 | 详情 |
| (IX) | 27687 | 3-amino-2-thiophenecarboxylic acid | C5H5NO2S | 详情 | 详情 |