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【结 构 式】 
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【分子编号】27653 【品名】7-benzyl-2-[[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino]-1-methyl-8-(4-methylpentyl)-1,7-dihydro-6H-purin-6-one 【CA登记号】 |
【 分 子 式 】C24H35N5O2 【 分 子 量 】425.5744 【元素组成】C 67.74% H 8.29% N 16.46% O 7.52% |
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：(VI)The acylation of 6-amino-5-(benzylamino)-2-methylpyrimidine-2,4(1H,3H)-dione (I) with 5-methylhexanoic acid (II) by means of EDCI and DMAP gives the amide (III), which is cyclized by means of hot POCl3 affording the chloropurin-6-one (IV). The condensation of (IV) with the chiral aminoalcohol (V) by means of DIEA and NMP yields intermediate (VI), which is cyclized by means of SOCl2 in dichloromethane providing the imidazo-purine (VII). Finally, this compound is debenzylated with ammonium formate and Pd(OH)2.
| 【1】 Ho, G.D.; Silverman, L.; Bercovivi, A.; Puchalski, C.; Tulshian, D.; Xia, Y.; Czarniecki, M.; Green, M.; Cleven, R.; Zhang, H.; Fawzi, A.; Synthesis and evaluation of potent and selective c-GMP phosphodiesterase inhibitors. Bioorg Med Chem Lett 1999, 9, 1, 7. |
| 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) | 27648 | 6-amino-5-(benzylamino)-3-methyl-2,4(1H,3H)-pyrimidinedione | C12H14N4O2 | 详情 | 详情 | |
| (II) | 27649 | 5-methylhexanoic acid | 628-46-6 | C7H14O2 | 详情 | 详情 |
| (III) | 27650 | N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-N-benzyl-5-methylhexanamide | C19H26N4O3 | 详情 | 详情 | |
| (IV) | 27651 | 7-benzyl-2-chloro-1-methyl-8-(4-methylpentyl)-1,7-dihydro-6H-purin-6-one | C19H23ClN4O | 详情 | 详情 | |
| (V) | 27652 | (2R)-2-amino-3-methyl-1-butanol; (R-(-))-Valinol; D-Valinol | 4276-09-9 | C5H13NO | 详情 | 详情 |
| (VI) | 27653 | 7-benzyl-2-[[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino]-1-methyl-8-(4-methylpentyl)-1,7-dihydro-6H-purin-6-one | C24H35N5O2 | 详情 | 详情 | |
| (VII) | 27654 | (7R)-3-benzyl-7-isopropyl-5-methyl-2-(4-methylpentyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one | C24H33N5O | 详情 | 详情 |
Extended Information