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【结 构 式】 
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【分子编号】27933 【品名】5-methylfuro[2,3-d]pyrimidine-2,4-diamine 【CA登记号】 |
【 分 子 式 】C7H8N4O 【 分 子 量 】164.16688 【元素组成】C 51.21% H 4.91% N 34.13% O 9.75% |
合成路线1
该中间体在本合成路线中的序号：(IV)Condensation of 2,6-diamino-4-hydroxypyrimidine (I) with chloroacetone (II) produced a mixture of pyrrolopyrimidine (III) and furopyrimidine (IV). After treatment of this mixture with pivalic anhydride, the insoluble pivaloyl amide of pyrrolopyrimidine (V) was separated from the soluble dipivaloyl furopyrimidine with boiling EtOAc. Subsequent Mannich reaction of (V) with dimethylamine and formaldehyde afforded the (dimethylamino)methyl derivative (VI). The dimethylamino group of (VI) was then displaced with 4-mercaptopyridine (VII) to give thioether (VIII). Finally, the pivaloyl amide group of (VIII) was hydrolyzed with NaOH to yield the target compound.
| 【1】 Gangjee, A.; et al.; 2-Amino-4-oxo-5-substituted-pyrrolo[2,3-d.]pyrimidines as nonclassical antifolate inhibitors of thymidylate synthase. J Med Chem 1996, 39, 23, 4563-4568. |
| 【2】 Gangjee, A.; et al.; Synthesis of classical and a nonclassical 2-amino-4-oxo-6-methyl-5-substituted Pyrrolo[2,3-d]pyrimidine antifolate inhibitors of thymidylate synthase1. J Med Chem 1999, 42, 12, 2272. |
| 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) | 14227 | N-Hydroxy-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxamide | C10H10N2O3 | 详情 | 详情 | |
| (II) | 15288 | 1-Chloroacetone; Chloroacetone | 78-95-5 | C3H5ClO | 详情 | 详情 |
| (III) | 27932 | 2-amino-6-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one | C7H8N4O | 详情 | 详情 | |
| (IV) | 27933 | 5-methylfuro[2,3-d]pyrimidine-2,4-diamine | C7H8N4O | 详情 | 详情 | |
| (V) | 27934 | 2,2-dimethyl-N-(6-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)propanamide | C12H16N4O2 | 详情 | 详情 | |
| (VI) | 27935 | N-[5-[(dimethylamino)methyl]-6-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethylpropanamide | C15H23N5O2 | 详情 | 详情 | |
| (VII) | 27936 | 4-Mercaptopyridine; 4-pyridinethiol | 4556-23-4 | C5H5NS | 详情 | 详情 |
| (VIII) | 27937 | 2,2-dimethyl-N-[6-methyl-4-oxo-5-[(4-pyridinylsulfanyl)methyl]-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]propanamide | C18H21N5O2S | 详情 | 详情 |