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Bropirimine, PNU-54461, U-54461, ABPP, Remisar

溴匹立明Chemical Name: 2-Amino-5-bromo-6-phenyl-4(3H)-pyrimidinone
CAS No. 56741-95-8
项目整合开发状态: Pre-Registered
项目研究机构: Pfizer (Originator), Yakult Honsha (Licensee)
合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.

合成路线:ABmFPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine (IV) with ethyl 3-(3-fluorophenyl)-3-oxopropanoate (III) (1,2,4).Ethyl 3-(3-fluorophenyl)-3-oxopropanoate (III) is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate (I) at 78 C with 3-fluorobenzoyl chloride (II) (3).Reaction of the resultant beta-ketoester with guanidine (IV) in refluxing ethanol affords its pyrimidinone (V) in high yield.ABmFPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.
📌 参考资料/链接:
参考文献标题:ABPP
文献作者:Wierenga,W.
参考来源:Drugs Fut 1984,9(8),567

📄 详细内容


合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.

合成路线:ABmFPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine (IV) with ethyl 3-(3-fluorophenyl)-3-oxopropanoate (III) (1,2,4).Ethyl 3-(3-fluorophenyl)-3-oxopropanoate (III) is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate (I) at 78 C with 3-fluorobenzoyl chloride (II) (3).Reaction of the resultant beta-ketoester with guanidine (IV) in refluxing ethanol affords its pyrimidinone (V) in high yield.ABmFPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.

参考文献标题:5-Substituted 2-amino-6-phenyl-4(3H)-pyrimidinones.Antiviral- and interferon-inducing agents
文献作者:Wierenga,W.; Skulnick,H.I.; Stringfellow,D.A.; Weed,S.D.; Renis,H.E.; Eidson,E.E.
参考来源:J Med Chem 1980,23(3),237-239


合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.

参考文献标题:
文献作者:Wierenga,W.; Skulnick,H.I.
参考来源:J Org Chem 1979,44310


合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.

参考文献标题:Triazines and related products.XV.2,4-Diaminopyrimidines and 2-aminopyrimidin-4(3H)-ones bearing 1,2,3-benzotriazinyl groups as potential dihydrofolic reductase inhibitors
文献作者:Brown,T.B.; Stevens,M.F.G.
参考来源:J Chem Soc - Perkins Trans I 1975,(11),1023-1028


合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.

参考文献标题:Antiviral and interferon induction stucture-activity relationship profile of 6-aryl-pyrimidines
文献作者:Skulnick,H.I.; Stringfellow,D.A.; Wierenga,W.; Weed,S.D.
参考来源:Am Soc Microbiol 1980,21402-1404


合成路线:ABPP is a phenylpyrimidinone and as such is prepared in high yield by condensation of guanidine with ethyl benzoylacetate.Ethyl benzoylacetate is commercially available and can also be prepared in high yield by condensation of dilithiomonoethylmalonate at 78 C with benzoyl chloride.Reaction of the resultant beta-ketoester with guanidine in refluxing ethanol affords its pyrimidinone in high yield.ABPP can be prepared from this pyrimidinone by bromination in acetic acid at room temperature.Similarly,iodine can be introduced at this step to afford the iodo analogue,AIPP.The overall yield of these pyrimidinones from monoethylmalonate is generally) 50%.
参考文献标题:High-perfomance liquid chromatographic determination of 5-halopyrimidinone interferon inducers
文献作者:Fitzpatrick,F.A.; Wynalda,M.A.
参考来源:Anal Chem 1982,17151


产品链接: CAS No. 56741-95-8››