【结 构 式】 |
【分子编号】44183 【品名】6-amino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C11H11N3O2 【 分 子 量 】217.22736 【元素组成】C 60.82% H 5.1% N 19.34% O 14.73% |
合成路线1
该中间体在本合成路线中的序号:(IV)Acylation of urea derivative (I) with cyanoacetic acid (II) in HOAc in the presence of Ac2O yields derivative (III), which is then cyclized by treatment with NaOH to provide (IV). Nitrosation of (IV) with NaNO2 and HCl affords nitroso derivative (V), which is then hydrogenated over Pd/C in EtOH to furnish substituted pyrimidinedione (VI). Finally, (VI) is coupled to Trolox (VII) with N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDC·HCl) and 1-hydroxybenzotriazole (HOBt) in DMF or with 4-(dimethylamino)pyridine (DMAP) and N-dicyclohexylcarbodiimide (DCC) in CH2Cl2 to yield the target compound.
【2】 Isobe, Y.; Goto, Y.; Tobe, M.; Takahashi, O. (Japan Energy Corp.); Hydroquinone derivs. and their medicinal use. JP 1998147575; US 5821247 . |
【1】 Matsui, J.; Tsuchiya, M.; Hayashi, H.; Goto, Y.; Hirota, K.; Obara, f.; Isobe, Y.; Tobe, M.; Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction. Bioorg Med Chem 2000, 8, 8, 2037. |
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) | 44181 | N-methyl-N'-phenylurea | 1007-36-9 | C8H10N2O | 详情 | 详情 |
(II) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
(III) | 44182 | N-(2-cyanoacetyl)-N-methyl-N'-phenylurea | C11H11N3O2 | 详情 | 详情 | |
(IV) | 44183 | 6-amino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H11N3O2 | 详情 | 详情 | |
(V) | 44184 | 6-amino-3-methyl-5-nitro-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H10N4O4 | 详情 | 详情 | |
(VI) | 44185 | 5,6-diamino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H12N4O2 | 详情 | 详情 | |
(VII) | 34833 | (2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acid | C14H18O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(I)Nitrosation of pyrimidinedione (I) with NaNO2/HCl affords (II), which is further reduced to the diaminopyrimidine (III) by catalytic hydrogenation over Pd/C. Subsequent coupling of (III) with 2,6-di-tert-butyl-4-hydroxycinnamic acid (IV) employing DPP-Cl furnishes the title amide
【1】 Isobe, Y.; Tobe, M.; Inoue, Y.; Goto, Y.; Obara, F.; Isobe, M.; Hayashi, H.; Inhibitory activities of novel pyrimidine derivatives on the contact hypersensitivity reaction. Chem Pharm Bull 2003, 51, 3, 309. |
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) | 44183 | 6-amino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H11N3O2 | 详情 | 详情 | |
(II) | 63475 | 6-amino-3-methyl-5-nitroso-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H10N4O3 | 详情 | 详情 | |
(III) | 44185 | 5,6-diamino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H12N4O2 | 详情 | 详情 | |
(IV) | 43375 | (E)-3-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-propenoic acid | 22014-01-3 | C17H24O3 | 详情 | 详情 |