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【结 构 式】 
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【分子编号】37137 【品名】6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinylformamide 【CA登记号】 |
【 分 子 式 】C8H12N4O3 【 分 子 量 】212.20844 【元素组成】C 45.28% H 5.7% N 26.4% O 22.62% |
合成路线1
该中间体在本合成路线中的序号：(X)The reaction of N-propylurea (V) with cyanacetic acid (VI) in hot acetic anhydride gives N-propyl-N'-cyanacetylurea (VII), which is nitrosated with NaNO2 - HCl yielding the isonitroso derivative (VIII). The reduction and simultaneous formylation of (VIII) with Zn in formic acid affords the formylamino compound (IX), which is cyclized by treatment with NaOH to give 6-amino-5-formylamino-1-propylpyrimidine-2,4-dione (X). Finally, this compound is cyclized by treatment with refluxing formic acid. The cyclization of (VII) with NaOH in hot water gives 6-amino-1-propylpyrimidine-2,4-dione (XI), which is nitrosated with NaNO2 - HCl as usual yielding 6-amino-nitroso-1-propylpyrimidine-2,4-dione (XII). The reduction of (XII) with H2 over Pt in DMF affords 5,6-diamino-1-propylpyrimidine-2,4-dione (XIII), which is finally formylated with refluxing formic acid to (X). This compound can also be finally cyclized by treatment with NaOH in refluxing water.
| 【1】 Ohtsuka, Y.; Oxazolopyrimidines. VI. Formation of 3-substituted xanthines via 7-(6H)-iminooxazolopyrimidines. Bull Chem Soc Jpn 1973, 46, 2, 506-509. |
| 【2】 Kjellin, P.G.; Persson, C.G.A. (Draco Läkemedel AB); Method and pharmaceutical preparation for treating chronic obstructive airway disease and cardiac disease, and intermediates for the preparation of therapeutically active xanthine derivs.. EP 0011609 . |
| 【3】 Sneddon, J.M.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Enprofylline. Drugs Fut 1982, 7, 9, 623. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 37133 | N-propylurea | C4H10N2O | 详情 | 详情 | |
| (VI) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
| (VII) | 37134 | N-(2-cyanoacetyl)-N'-propylurea | C7H11N3O2 | 详情 | 详情 | |
| (VIII) | 37135 | N-[2-cyano-2-(hydroxyimino)acetyl]-N'-propylurea | C7H10N4O3 | 详情 | 详情 | |
| (IX) | 37136 | N-[2-cyano-2-(formylamino)acetyl]-N'-propylurea | C8H12N4O3 | 详情 | 详情 | |
| (X) | 37137 | 6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinylformamide | C8H12N4O3 | 详情 | 详情 | |
| (XI) | 37138 | 6-amino-1-propyl-2,4(1H,3H)-pyrimidinedione | C7H11N3O2 | 详情 | 详情 | |
| (XII) | 37139 | 6-amino-5-nitroso-1-propyl-2,4(1H,3H)-pyrimidinedione | C7H10N4O3 | 详情 | 详情 | |
| (XIII) | 20546 | 5,6-diamino-1-propyl-2,4(1H,3H)-pyrimidinedione | C7H12N4O2 | 详情 | 详情 |