(4,6-二甲氧基嘧啶-2-基)脲 | 151331-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4,6-二甲氧基嘧啶-2-基)脲
• 中文别名: N-(4,6-二甲氧基-2-嘧啶基)脲
• 英文名称: (4,6-dimethoxypyrimidin-2-yl)urea
• 英文别名: 4,6-Dimethoxy-2-pyrimidinyl urea
• CAS: 151331-81-6
• 化学式: C₇H₁₀N₄O₃
• 分子量: 198.181
• InChiKey: BNOVYBVKWYHEMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4,6-二甲氧基嘧啶-2-基)脲 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 环己烷 为溶剂， 反应 2.0h， 以90%的产率得到{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl chloride
  参考文献：
  名称：

  一种烟嘧磺隆原药的合成方法

  摘要：

  本发明提供了一种烟嘧磺隆原药的合成方法，其包括以下四步：N,N‑二甲基烟酰胺的合成、N,N‑二甲基烟酰胺的氧化、2‑脲基‑4，6‑二甲氧基嘧啶的磺酰化和烟嘧磺隆原药的合成，所以，该合成方法路线比较短，从而使得成本比较低；上述原药的合成方法的收率高、且合成条件温合、避免了使用高毒高污染的三氯氧磷、氯气、光气等原料，绿色安全，可实现工业化生产。

  公开号：

  CN108558830B
• 作为产物：
  描述：

  2-氯-4,6-二甲氧基嘧啶 在 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 、 palladium diacetate 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 生成 (4,6-二甲氧基嘧啶-2-基)脲
  参考文献：
  名称：

  Synthesis of Unsymmetrical Diarylureas via Pd-Catalyzed C–N Cross-Coupling Reactions

  摘要：

  A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.

  DOI：

  10.1021/ol201210t

文献信息

• Sultamsulfonamide derivatives and herbicides
  申请人：NISSAN CHEMICAL INDUSTRIES LTD.

  公开号：EP0342456A2

  公开（公告）日：1989-11-23

  A sultamsulfonamide derivative having the formula: wherein Q is or wherein each of R1, R2, R3, R4 and Rs is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, trifluoromethyl, nitro, cyano, amino, C1-C6 alkoxy, phenoxy (provided that this phenoxy may be substituted by halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxycarbonyl), C1-C6 alkylthio, phenylthio (provided that this phenylthio may be substituted by halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxycarbonyl), C1-C6 alkylsulfonyl, benzenesulfonyl (provided that this benzenesulfonyl may be substituted by halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxycarbonyl), C1-C6 alkylcarbonyl, carboxylic acid, C1 -C6 alkoxycarbonyl, C1-C6 monoalkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C2-C6 acylamino, C1-C6 halogenoalkyl, C1-C6 alkyl substituted by cyano, C1-C6 alkyl substituted by hydroxyl, C1-C6 alkyl substituted by amino, C1-C6 alkyl substituted by C1-C6 alkoxy, C1-C6 alkyl substituted by C1-C6 halogenoalkoxy, Cl-C6 alkyl substituted by C1-C6 alkylthio, C1-C6 alkyl substituted by C1-C6 alkylsulfonyl, C1-C6 alkyl substituted by C1-C6 alkylcarbonyl, C1-C6 alkyl substituted by carboxylic acid, Ci-C6 alkyl substituted by C1-C6 alkoxycarbonyl, C1-C6 alkyl substituted by C2-C6 alkenyloxy, C1-C6 alkyl substituted by C2-C6 alkynyloxy, C1-C6 alkyl substituted by C2-C6 acylamino, C1-C6 alkyl substituted by C1-C6 alkylsulfonyloxy, C2-C6 alkenyl substituted by C1-C6 alkoxycarbonyl, C2-C6 alkynyl substituted by cyano, phenyl (provided that this phenyl may be substituted by halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxycarbonyl) or C1-C6 alkyl substituted by phenyl (provided that this phenyl may be substituted by halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxycarbonyl); X is oxygen or sulfur; M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl cr C2-C6 alkynyl; and G is wherein A is CH or nitrogen, and each of B and C is C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halogenoalkyl, C1-C4 halogenoalkoxy, halogen or C1-C4 monoalkylamino, or an agriculturally useful salt thereof.

  苏丹磺酰胺衍生物，其式如下 其中 Q 是 或 其中 R1、R2、R3、R4 和 Rs 各为氢、C1-C6 烷基、C2-C6 烯基、C2-C6 炔基、卤素、三氟甲基、硝基、氰基、氨基、C1-C6 烷氧基、苯氧基（条件是该苯氧基可被卤素取代、C1-C6烷硫基、苯硫基（条件是该苯硫基可被卤素、三氟甲基、C1-C6 烷基、C1-C6 烷氧基或 C1-C6 烷氧羰基取代）、C1-C6烷基磺酰基、苯磺酰基（但苯磺酰基可被卤素、三氟甲基、C1-C6 烷基、C1-C6 烷氧基或 C1-C6 烷氧羰基取代）、C1-C6 烷基羰基、羧酸、C1-C6 烷氧羰基、C1-C6 单烷基氨基羰基、C1-C6 二烷基氨基羰基、C2-C6 氨基酰基、C1-C6 卤代烷基、被氰基取代的 C1-C6 烷基、被羟基取代的 C1-C6 烷基、被氨基取代的 C1-C6 烷基、被 C1-C6 烷氧基取代的 C1-C6 烷基、被 C1-C6 卤代烷氧基取代的 C1-C6 烷基、被 C1-C6 烷硫基取代的 C1-C6 烷基、被 C1-C6 烷磺酰基取代的 C1-C6 烷基、被 C1-C6 烷羰基取代的 C1-C6 烷基、被羧酸取代的 C1-C6 烷基、被 C1-C6 烷氧羰基取代的 Ci-C6 烷基、被 C2-C6 烯氧基取代的 C1-C6 烷基、被 C2-C6 烷炔氧基取代的 C1-C6 烷基、被 C2-C6 氨基酰基取代的 C1-C6 烷基、被 C1-C6 烷基磺酰氧基取代的 C1-C6 烷基、被 C1-C6 烷氧基羰基取代的 C2-C6 烯基、被氰基取代的 C2-C6 烷炔基、苯基（条件是该苯基可被卤素、三氟甲基、C1-C6 烷基、C1-C6 烷氧基或 C1-C6 烷氧基羰基取代）或被苯基取代的 C1-C6 烷基（条件是该苯基可被卤素、三氟甲基、C1-C6 烷基、C1-C6 烷氧基或 C1-C6 烷氧基羰基取代）；X 是氧或硫；M 是氢、C1-C6 烷基、C2-C6 烯基或 C2-C6 烷炔基；G 是 其中 A 是 CH 或氮，B 和 C 分别是 C1-C4 烷基、C1-C4 烷氧基、C1-C4 卤代烷基、C1-C4 卤代烷氧基、卤素或 C1-C4 单烷基氨基，或其农业上有用的盐。
• Verfahren zur Herstellung von Sulfonylharnstoffsalzen
  申请人：Novartis AG

  公开号：EP0916660A2

  公开（公告）日：1999-05-19

  Verbindungen der Formel I, worin R1 CO2CH3, CON(CH3)2, OCH2CF3, N(CH3)COCH3, N(CH3)SO2CH3, CF3 oder SO2C2H5; R2 Wasserstoff oder CF3; und M Natrium oder Kalium bedeutet, werden hergestellt, indem man eine Verbindung der Formel IV in einem aprotischen organischen Lösungsmittel entweder mit einer Verbindung der Formel V umsetzt, oder mit NH3 in einem aprotischen organischen Lösungsmittel in die Verbindung der Formel III überführt, diese mit einem Hydrid, Hydroxid, Alkoholat, Hydrogencarbonat oder Carbonat von Natrium oder Kalium in einem aprotischen organischen Lösungsmittel zur Verbindung der Formel II umsetzt, und diese anschließend mit einer Verbindung der Formel VI worin R1 und R2 die unter Formel I angegebene Bedeutung haben, umsetzt.

  一种式 I 的化合物 其中 R1 是 CO2CH3、CON(CH3)2、OCH2CF3、N(CH3)COCH3、N(CH3)SO2CH3、CF3 或 SO2C2H5；R2 是氢或 CF3；M 是钠或钾。 在非沸腾有机溶剂中与式 V 的化合物反应 或与 NH3 在非沸腾有机溶剂中反应，得到式 III 化合物 与氢化物、氢氧化物、醇酸盐、碳酸氢盐或碳酸钠或碳酸钾在非沸腾有机溶剂中反应，得到式 II 化合物 然后与式 VI 的化合物反应 其中 R1 和 R2 具有式 I 中给出的含义。
• Process for preparation of sulfonylurea salts
  申请人：——

  公开号：US20010008938A1

  公开（公告）日：2001-07-19

  Compounds of formula 1, 1 wherein R 1 is CO 2 CH 3 , CON(CH 3 ) 2 , OCH 2 CF 3 , N(CH 3 )COCH 3 , N(CH 3 )SO 2 CH 3 , CF 3 or SO 2 C 2 H 5 ; R 2 is hydrogen or CF 3 ; and M is sodium or potassium are prepared by reacting a compound of formula IV 2 in an aprotic, organic solvent either with a compound of formula V 3 or with NH 3 in an aprotic, organic solvent to form a compound of formula III 4 reacting this with a hydride, hydroxide, alcoholate, hydrogen carbonate or carbonate of sodium or potassium in an aprotic, organic solvent to form a compound of formula II 5 and then with a compound of formula VI 6 wherein R 1 and R 2 are as defined under formula I.

  式 1 的化合物、 1 其中 R 1 是 CO 2 CH 3 、CON(CH 3 ) 2 , OCH 2 CF 3 N(CH 3 ) COCH 3 N(CH 3 ) SO 2 CH 3 ，CF 3 或 SO 2 C 2 H 5 ; R 2 是氢或 CF 3 和 M 为钠或钾的化合物，通过反应制备式 IV 2 在非沸腾有机溶剂中与式 V 3 或 NH 3 在壬烷有机溶剂中生成式 III 化合物 4 与氢化物、氢氧化物、醇酸盐、碳酸氢盐或碳酸钠或碳酸钾在壬烷有机溶剂中反应， 形成式 II 的化合物 5 然后与式 VI 的化合物反应 6 其中 R 1 和 R 2 如式 I 所定义。
• Structural Elucidation of Phototransformation Products of Azimsulfuron in Water
  作者：M. Vittoria Pinna、Michele Zema、Carlo Gessa、Alba Pusino

  DOI：10.1021/jf070897k

  日期：2007.8.1

  The photodegradation of the sulfonylurea herbicide azimsulfuron, N-[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (AZS), was studied in water at different wavelengths and in the presence of photocatalysts. AZS was rapidly degraded by UV light, affording three photoproducts. The main product, accounting for about 70% of photodegraded herbicide, was identified as 6-amino-5-[(4,6-dimethoxypyrimidin-2-yl)methylamino]-1,5,6,8-tetrahydro-7-oxa-8 lambda(6)-tia-1,2,5,6-tetraza-azulen-4-one (ADTA) by single-crystal X-ray diffraction. With simulated sunlight irradiation, the reaction was slower and 2-amino-4,6-dimethoxypyrimidine (DPA) and 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (MPS), arising from a photohydrolytic cleavage of the sulfonylurea bridge, were the only byproducts observed. The reactions followed first-order kinetics. The addition of dissolved organic matter (DOM) did not modify significantly the AZS photodegradation rate. The presence of Fe2O3 accelerated more than twice the reaction rate affording two major products, DPA and MPS, together with minor amounts of N-[[(5-hydroxy-4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (AZS-OH). The greatest degradation rate was detected in the presence of TiO2. Only the photohydroxylation product AZS-OH was observed, which was transformed rapidly into oxalic acid.
• Chromatography and High-Resolution Mass Spectrometry for the Characterization of the Degradation Products of the Photodegradation of Amidosulfuron: An Analytical Approach
  作者：Mourad Harir、Amina Chnirheb、Basem Kanawati、Mohammed El Azzouzi、Philippe Schmitt-Kopplin

  DOI：10.1021/jf400133w

  日期：2013.6.5

  Simulated sunlight irradiation causing degradation of amidosulfuron, a pyrimidinylsulfonylurea herbicide, has been investigated in aqueous solution. The main degradation products were followed up by ultrahigh-pressure liquid chromatography with a UV detector (UHPLC-UV) and identified by combining ultrahight-pressure liquid chromatography-mass spectrometry (UHPLC-MS) and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS). On the basis of the retrosynthetic analysis, the most identified degradation products were mainly due to the losses of methylsulfamic acid (CH5NO3S), sulfocarbamic acid (CH3NO5S), carbamic acid (CH3NO2), methyl(methylsulfonyl)sulfamic acid (C2H7NO5S2), N-methylmethanesulfonamide (C2H7NO2S), and sulfonic acid (H2SO4) molecules. Accordingly, O and S-demethylation as well as hydroxylation processes were also observed. Sum formulas of the main degradation products were assigned, and a mechanical pathway is proposed.