CAS: 132973-51-4; Dimethyl 2-(Methylthio)-4,5-Pyrimidinedicarboxylate

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166392-24-1 2092628-15-2 111253-04-4

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CAS号762-42-5 丁炔二酸二甲酯 | CAS号132973-52-5 trimethyl 4-(di...

📜4-Dimethylamino-2-Methylsulfanyl-4H-Pyrimidine-1,5,6-Tricarboxylic Acid Trimethyl Ester 以 苯 用作溶剂,化学反应 24.0H,反应生成2-甲硫基-4,5-嘧啶二甲酸二甲酯
参考文献:1,3-Diaza-1,3-Butadienes. Synthesis And Conversion Into Pyrimidines By [4π + 2π] Cycloaddition With Electron Deficient Acetylenes. Synthetic Utility Of 2-(Trichloromethyl)Pyrimidines1
标题:1,3-Diaza-1,3-Butadienes. Synthesis And Conversion Into Pyrimidines By [4π + 2π] Cycloaddition With Electron Deficient Acetylenes. Synthetic Utility Of 2-(Trichloromethyl)Pyrimidines1
摘要:Methods Have Been Devised To Generate 1H-1,3-Diaza-1,3-Butadienes Bearing A Leaving Group At Position-4 In Latent,Masked,And Unprotected Forms. A Hallmark Of These Azadienes Is That They Undergo Thermal [4 Pi + 2 Pi] Cycloaddition Reactions With Electron Deficient Acetylenes To Give Adducts Which Are Aromatized To Pyrimidine Derivatives Under The Reaction Conditions. Thus,1-(Methoxycarbonyl)-3-Acylamidines 17 On Beating In Solution Are Converted In Situ Into The 1,3-Diaza-1,3-Dienes 18 And/or 19 Which React With Dimethyl Acetylenedicarboxylate (Dmad) To Produce The Pyrimidines 20. The 1-Boc-1,3-Diaza-1,3-Dienes 24 Are Masked Forms Of The Lh-Dienes Inasmuch As They React With Dmad Under Relatively Mild Conditions To Give The Dihydropyrimidine Adducts 25,Which Are Easily Detectable By H-1 NMR Spectroscopy,And Which Aromatize To Pyrimidines 26 At Higher Temperatures. The 4-Methylthio Compounds 31 And 33,And The 2-(Trichloromethyl) Compounds 37,Are Isolable,Relatively Stable,1H-1,3-Diaza-1,3-Butadienes,These Easily Prepared Compounds React With Electron Deficient Acetylenes Under Mild Conditions To Provide The Pyrimidines 20,34,And 38,Respectively,In Fair To Excellent Yields. The 2-(Trichloromethyl)Pyrimidines 38 Are Very Useful Precursors Of A Wide Variety Of Other 2-Substituted Pyrimidines 46-52.
Doi:10.1021/jo952106W