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【结 构 式】 
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【分子编号】60891 【品名】N-(2-chlorobenzyl)-4,6-diiodo-N-methyl-5-pyrimidinamine; N-(2-chlorobenzyl)-N-(4,6-diiodo-5-pyrimidinyl)-N-methylamine 【CA登记号】 |
【 分 子 式 】C12H10ClI2N3 【 分 子 量 】485.49326 【元素组成】C 29.69% H 2.08% Cl 7.3% I 52.28% N 8.66% |
合成路线1
该中间体在本合成路线中的序号：(X)Iodination of 5-amino-4,6-dichloropyrimidine (VI) by means of NaI in concentrated HI affords the diiodopyridine (VII). Sequential alkylation of aminopyrimidine (VII) with 2-chlorobenzyl bromide (VIII) to produce (IX), and further N-methylation with iodomethane and NaH, lead to the tertiary amine (X). Ammonolysis of the diiodopyrimidine (X) with ethanolic ammonia in a sealed tube at 80 C yields amine (XI). Finally, Sonogashira coupling between acetylene (V) and iodopyrimidine (XI) in the presence of Pd(PPh3)2Cl2 and CuI furnishes the target diaryl acetylene
| 【1】 Gomtsyan, A.; et al.; Design, synthesis, and structure-activity relationship of 6-alkynylpyrimidines as potent adenosine kinase inhibitors. J Med Chem 2002, 45, 17, 3639. |
| 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) | 60888 | 4-(5-ethynyl-2-pyridinyl)morpholine | C11H12N2O | 详情 | 详情 | |
| (VI) | 22845 | 5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine | 5413-85-4 | C4H3Cl2N3 | 详情 | 详情 |
| (VII) | 60889 | 4,6-diiodo-5-pyrimidinamine; 4,6-diiodo-5-pyrimidinylamine | C4H3I2N3 | 详情 | 详情 | |
| (VIII) | 53082 | 1-(Bromomethyl)-2-chlorobenzene; 2-Chloro-alpha-bromotoluene; 2-Chlorobenzyl bromide; Alpha-Bromo-2-chlorotoluene; o-Chlorobenzyl bromide | 611-17-6 | C7H6BrCl | 详情 | 详情 |
| (IX) | 60890 | N-(2-chlorobenzyl)-4,6-diiodo-5-pyrimidinamine; N-(2-chlorobenzyl)-N-(4,6-diiodo-5-pyrimidinyl)amine | C11H8ClI2N3 | 详情 | 详情 | |
| (X) | 60891 | N-(2-chlorobenzyl)-4,6-diiodo-N-methyl-5-pyrimidinamine; N-(2-chlorobenzyl)-N-(4,6-diiodo-5-pyrimidinyl)-N-methylamine | C12H10ClI2N3 | 详情 | 详情 | |
| (XI) | 60892 | N-(4-amino-6-iodo-5-pyrimidinyl)-N-(2-chlorobenzyl)-N-methylamine; N~5~-(2-chlorobenzyl)-6-iodo-N~5~-methyl-4,5-pyrimidinediamine | C12H12ClIN4 | 详情 | 详情 |