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【结 构 式】

【分子编号】48659

【品名】5-fluoro-3-(2-methylbenzoyl)-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【 分 子 式 】C12H9FN2O3

【 分 子 量 】248.2135432

【元素组成】C 58.07% H 3.65% F 7.65% N 11.29% O 19.34%

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)

Atofluding can be prepared by several similar ways: a) Acylation of 5-fluorouracil (I) with acetic anhydride in refluxing pyridine gives 1-acetyl-5-fluorouracil (II), which is then acylated with 2-methylbenzoyl chloride (V) by means of either TEA in dioxane at room temperature or pyridine in dioxane at 80 C. b) Acylation of 5-fluorouracil (I) with 2-methylbenzoyl chloride (V) in pyridine at room temperature yields 5-fluoro-3-(2-methylbenzoyl)uracil (III), which is then acylated with acetic anhydride at 80 C or with acetic anhydride by means of TEA in cooled dioxane. c) Acylation of 5-fluorouracil (I) with acetyl chloride by means of TEA in dioxane at room temperature provides 1,3-diacetyl-5-fluorouracil (IV), which is then acytated with 2-methylbenzoyl chloride (V) by means of TEA in dioxane.

1 Kametani, T.; Hiiragi, M.; Kigasawa, K.; et al.; Studies on the synthesis of chemotherapeutics. 10. Synthesis and antitumor activity of N-acyl- and N-(alkoxycarbonyl)-5-fluorouracil derivatives. J Med Chem 1980, 23, 12, 1324.
2 Castaner, J.; Zhang, Z.; Xu, W.; Atofluding. Drugs Fut 2001, 26, 10, 935.
3 Okada, T.; Uracil derivs., process for preparing the same, and oncotic preparation thereof. JP 1979135782; WO 7900922 .
4 Palleja Martinez, J.; Okada, T.; Process to obtain new 5-fluorouracil derivs., specifically N1-acyl-substd.-N3-ortho-toluyl-5-fluorouracils. ES 2015772 .
5 Hoffer, M. (Hoffmann-La Roche, Inc.); Preparation of thymidine and deoxyfluorouridine, and intermediates therefor. US 2949451 .
6 Okada, T.; Palleja Martinez, J.; Process to obtain a new 5-fluorouracil deriv.. ES 2015151 .
7 Hoffer, M. (Hoffmann-La Roche, Inc.); Mercury salts of nitrogen heterocyclics and preparation thereof. US 3041335 .
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) 29241 5-fluoro-2,4(1H,3H)-pyrimidinedione;5-fluorouracil;5-Fluoro-2,4-pyrimidinedione;5-Fluoropyrimidine-2,4-dione 51-21-8 C4H3FN2O2 详情 详情
(II) 48658 1-acetyl-5-methyl-2,4(1H,3H)-pyrimidinedione C7H8N2O3 详情 详情
(III) 48659 5-fluoro-3-(2-methylbenzoyl)-2,4(1H,3H)-pyrimidinedione C12H9FN2O3 详情 详情
(IV) 48660 1,3-diacetyl-5-fluoro-2,4(1H,3H)-pyrimidinedione C8H7FN2O4 详情 详情
(V) 14770 2-methylbenzoyl chloride; o-Toluoyl chloride 933-88-0 C8H7ClO 详情 详情
Extended Information