Atofluding, A-OT

1-乙酰基-3,2-甲苯甲酰基-5-氟尿嘧啶Chemical Name: 1-Acetyl-5-fluoro-3-(2-methylphenyl)uracil; 1-Acetyl-5-fluoro-3-(2-methylbenzoyl)pyrimidine-2,4(1H,3H)-dione
CAS No. 71861-76-2
项目整合开发状态: Phase III
项目研究机构: Xian Lijun Pharmaceutical (Originator), Taiho (Not Determined)
合成路线: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.
📌 参考资料/链接:
参考文献标题:Uracil derivs.,process for preparing the same,and oncotic preparation thereof
文献作者:Okada,T.
参考来源:JP 1979135782; WO 7900922

📄 详细内容


合成路线: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.

参考文献标题:Preparation of thymidine and deoxyfluorouridine,and intermediates therefor
文献作者:Hoffer,M.(Hoffmann-La Roche,Inc.)
参考来源:US 2949451


合成路线: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.

参考文献标题:Mercury salts of nitrogen heterocyclics and preparation thereof
文献作者:Hoffer,M.(Hoffmann-La Roche,Inc.)
参考来源:US 3041335


合成路线: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.

参考文献标题:Process to obtain a new 5-fluorouracil deriv.
文献作者:Okada,T.; Palleja Mart韓ez,J.
参考来源:ES 2015151


合成路线: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.

参考文献标题:Process to obtain new 5-fluorouracil derivs.,specifically N1-acyl-substd.-N3-ortho-toluyl-5-fluorouracils
文献作者:Palleja Mart韓ez,J.; Okada,T.
参考来源:ES 2015772


合成路线: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.

参考文献标题:Studies on the synthesis of chemotherapeutics.10.Synthesis and antitumor activity of N-acyl- and N-(alkoxycarbonyl)-5-fluorouracil derivatives
文献作者:Kametani,T.; Kigasawa,K.; Hiiragi,M.; Wakisaka,K.; Haga,S.; Nagamatsu,Y.; Sugi,H.; Fukawa,K.; Irino,O.; Yamamoto,T.; Nishimura,N.; Taguchi,A.; Okada,T.; Nakayama,M.
参考来源:J Med Chem 1980,23(12),1324


合成路线: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.
参考文献标题:Atofluding
文献作者:Castar,J.; Zhang,Z.; Xu,W.
参考来源:Drugs Fut 2001,26(10),935


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