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【结 构 式】 
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【分子编号】43735 【品名】4-chloro-2,6-di(1-pyrrolidinyl)pyrimidine 【CA登记号】111669-15-9 |
【 分 子 式 】C12H17ClN4 【 分 子 量 】252.74664 【元素组成】C 57.03% H 6.78% Cl 14.03% N 22.17% |
合成路线1
该中间体在本合成路线中的序号：(II)The intermediate pyrimidine (IV) has been obtained as follows: The reaction of 2,4,6-trichloropyrimidine (I) with pyrrolidine in THF gives 6-chloro-2,4-bis(1-pyrrolidinyl) pyrimidine (II), which is condensed with piperazine (III) in pyridine to yield 6-(1-piperazinyl)-2,4-bis(1-pyrrolidinyl)pyrimidine (IV). The methylation of 21-acetoxy-pregna-1,4,9(11),16-tetraene-3,20-dione (V) with methylmagnesium chloride catalyzed by copper propionate, followed by hydrolysis of the acetate group with NaOMe in methanol, gives the 16-alpha-methyl steroid (VI), which is condensed with piperazine intermediate (IV) by means of MeSO2Cl and TEA in acetonitrile, affording the precursor (VII). Finally, this compound is treated with methanesulfonic acid to afford the target compound.
| 【1】 Braughler, J.M.; Hall, E.D.; Jacobsen, E.J.; McCall, J.M.; Means, E.D.; THE 21-AMINOSTEROIDS: POTENT INHIBITORS OF LIPID PEROXIDATION FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM TRAUMA AND ISCHEMIA. Drugs Fut 1989, 14, 2, 143. |
| 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) | 43734 | 2,4,6-trichloropyrimidine | 3764-01-0 | C4HCl3N2 | 详情 | 详情 |
| (II) | 43735 | 4-chloro-2,6-di(1-pyrrolidinyl)pyrimidine | 111669-15-9 | C12H17ClN4 | 详情 | 详情 |
| (III) | 10395 | 1,1,1-Triethoxypropane; 1,1-Diethoxypropyl ethyl ether; Triethyl orthopropionate | 115-80-0 | C9H20O3 | 详情 | 详情 |
| (IV) | 26075 | 4-(1-piperazinyl)-2,6-di(1-pyrrolidinyl)pyrimidine | C16H26N6 | 详情 | 详情 | |
| (V) | 43736 | 2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate | 37413-91-5 | C23H26O4 | 详情 | 详情 |
| (VI) | 43737 | (8S,10R,13S,14S,16R,17S)-17-glycoloyl-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one | C22H28O3 | 详情 | 详情 | |
| (VII) | 43738 | (8S,10R,13S,14S,16R,17S)-17-(2-[4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]acetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one | C38H52N6O2 | 详情 | 详情 |