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【结 构 式】

【分子编号】43819

【品名】6-amino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【 分 子 式 】C8H13N3O2

【 分 子 量 】183.21024

【元素组成】C 52.45% H 7.15% N 22.94% O 17.47%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Cyclization of N,N'-diethylurea (I) with cyanoacetic acid (II) in hot acetic anhydride gives 6-amino-1,3-diethyluracil (III) which is nitrosated with NaNO2/HOAc in water to yield 6-amino-1,3-diethyl-5-nitrosouracil (IV). The reduction of (IV) with Na2S2O4 and K2CO3 in concentrated aqueous ammonia affords 5,6-diamino-1,3-diethyluracil (V), which is condensed with either 3-(3,4-dimethoxyphenyl)-2(E)-propenoyl chloride (VI) in EtOH/water or 3-(3,4-dimethoxyphenyl)-2(E)-propenoic acid (VII) and 3-[3-(diethylamino)propyl]-1-ethylcarbodiimide (EDAC) in dioxane/water to provide the corresponding amide (VIII). Cyclization of (VIII) by means of NaOH in the same solvent furnishes the xanthine derivative (IX), which is finally methylated with methyl iodide and K2CO3 in DMF.

1 Blicke, F.F.; Godt, H.C. Jr.; Reactions of 1,3-dimethyl-5,6-diaminouracil. J Am Chem Soc 1954, 76, 2798.
2 Leeson, P.A.; Castañer, J.; Sorbera, L.A.; Martín, L.; Rabasseda, X.; KW-6002. Drugs Fut 2001, 26, 1, 21.
3 Shimada, J.; Koike, N.; Nonaka, H.; et al.; Adenosine A2A antagonists with potent anti-cataleptic activity. Bioorg Med Chem Lett 1997, 7, 18, 2349.
4 Suzuki, F.; Shimada, J.; Ishii, A.; Nakamura, J.; Ichikawa, S.; Kitamura, S.; Koike, N. (Kyowa Hakko Kogyo Co., Ltd.); Antidepressant. EP 0628311; JP 1994502746; WO 9401114 .
5 Suzuki, F.; Shimada, J.; Koike, N.; Nakamura, J.; Shiozaki, S.; Ichikawa, S.; Nonaka, H. (Kyowa Hakko Kogyo Co., Ltd.); Therapeutic agents for Parkinson's disease. EP 0590919; JP 1994211856; US 5484920 .
6 Miwa, K.; Ito, K.; Kato, N.; Kuge, Y.; Kousai, M.; Tomioka, S. (Kyowa Hakko Kogyo Co., Ltd.); Preparation of uracil derivs.. JP 1997040652 .
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) 43818 N,N'-diethylurea 623-76-7 C5H12N2O 详情 详情
(II) 12591 Cyanoacetic Acid; 2-Cyanoacetic acid 372-09-8 C3H3NO2 详情 详情
(III) 43819 6-amino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione C8H13N3O2 详情 详情
(IV) 43820 6-amino-1,3-diethyl-5-nitroso-2,4(1H,3H)-pyrimidinedione C8H12N4O3 详情 详情
(V) 28567 5,6-diamino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione C8H14N4O2 详情 详情
(VI) 33601 (E)-3-(3,4-dimethoxyphenyl)-2-propenoyl chloride C11H11ClO3 详情 详情
(VII) 28568 (E)-3-(3,4-dimethoxyphenyl)-2-propenoic acid 2316-26-9 C11H12O4 详情 详情
(VIII) 43821 (E)-N-(6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-3-(3,4-dimethoxyphenyl)-2-propenamide C19H24N4O5 详情 详情
(IX) 28569 8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-1H-purine-2,6-dione C19H22N4O4 详情 详情
Extended Information