4

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholi­nium chloride (DMTMM) is a highly effective coupling reagent used for both amide synthesis and for the preparation of esters.[1] [2] The advantages of using DMTMM as a coupling reagent include excellent product yields and the possibility that reactions can be performed in one step at room temperature and under atmospheric conditions.[1] Readily removed and solubilising solvents (e.g. MeOH, EtOH, i-PrOH) including water, can be used in reactions with DMTMM and no drying requirements are needed for the reaction solvents.[3] Furthermore, no additives are required and acids can be activated in situ.[2]

The by-product of the reaction with DMTMM (2-hydroxy-4,6-dimethoxy-1,3,5-triazine, HO-MDT) is highly water soluble and can be easily removed from the main reaction product.[2] [4] The recovered by-product can also be converted back into the starting material via 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT).

DMTMM is commercially available, but can also be prepared in a straightforward manner by reaction between CDMT and n-methylmorpholine (NMM) or from cyanuric chloride.[3] [5] The reagents for the preparation of ­DMTMM are inexpensive, providing an economical benefit when using this reagent.

中文翻译：

4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓氯化物（DMTMM）是用于酰胺合成和酯制备的高效偶联剂。[1] [2]使用DMTMM作为偶联剂的优势包括出色的产品收率，以及反应可以在室温和大气条件下一步进行的可能性。[ 1 ]易于除去和增溶的溶剂（例如MeOH，EtOH，i -PrOH）包括水，可用于与DMTMM的反应，反应溶剂无需干燥。[ 3 ]此外，不需要添加剂，酸可就地活化。[ 2 ]

与DMTMM的反应副产物（2-羟基-4,6-二甲氧基-1,3,5-三嗪，HO-MDT）具有很高的水溶性，可以很容易地从主要反应产物中除去。[2] [4]回收的副产物也可以通过2-氯-4,6-二甲氧基-1,3,5-三嗪（CDMT）转化回原料。

DMTMM是可商购的，但也可以通过CDMT与正甲基吗啉（NMM）之间的反应或由氰尿酰氯以直接的方式制备。[3] [5]用于制备DMTMM的试剂是廉价的，当使用该试剂时提供经济利益。