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【结 构 式】 
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【分子编号】19803 【品名】N-benzyl-N'-propylurea 【CA登记号】 |
【 分 子 式 】C11H16N2O 【 分 子 量 】192.26092 【元素组成】C 68.72% H 8.39% N 14.57% O 8.32% |
合成路线1
该中间体在本合成路线中的序号：(I)The cyclization of N-benzyl-N'-propylurea (I) with cyanacetic acid (II) in hot acetic anhydride gives 6-amino-1-benzyl-3-propyluracil (III), which is nitrosated with NaNO2/acetic acid and reduced with sodium dithionite to yield 5,6-diamino-1-benzyl-3-propyluracil (IV). The cyclization of (IV) with cyclopentylcarbonyl chloride (V) by means of NaOH in refluxing ethanol affords 3-benzyl-8-cyclopentyl-1-propylxanthine (VI), which is acylated with pivaloyl chloride (VII)/Na2CO3 in DMF giving the expected 7-acyl derivative (VIII). The debenzylation of (VIII) by hydrogenation over Pd/C as usual yields 8-cyclopentyl-7-pivaloyl-1-propylxanthine (IX), which is condensed with 1-bromo-3-fluoropropane (X) by means of Na2CO3 in DMF to afford 8-cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine (XI). Finally, this compound is deprotected with NaOH in DMSO/water.
| 【1】 Holschbach, M.H.; et al.; A1 adenosine receptor antagonists as ligands for positron emission tomography (PET) and single-photon emission tomography (SPET). J Med Chem 1998, 41, 4, 555. |
| 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) | 19803 | N-benzyl-N'-propylurea | C11H16N2O | 详情 | 详情 | |
| (II) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
| (III) | 19805 | 6-amino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione | C14H17N3O2 | 详情 | 详情 | |
| (IV) | 19806 | 5,6-diamino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione | C14H18N4O2 | 详情 | 详情 | |
| (V) | 19807 | 1,4-cyclopentadiene-1-carbonyl chloride | C6H5ClO | 详情 | 详情 | |
| (VI) | 19808 | 3-benzyl-8-cyclopentyl-1-propyl-3,7-dihydro-1H-purine-2,6-dione | C20H24N4O2 | 详情 | 详情 | |
| (VII) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (VIII) | 19810 | 3-benzyl-8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione | C25H32N4O3 | 详情 | 详情 | |
| (IX) | 19811 | 8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione | C18H26N4O3 | 详情 | 详情 | |
| (X) | 19812 | 1-bromo-3-fluoropropane | 352-91-0 | C3H6BrF | 详情 | 详情 |
| (XI) | 19813 | 8-Cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine | C21H31FN4O3 | 详情 | 详情 |